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[ CAS No. 5317-33-9 ]

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Chemical Structure| 5317-33-9
Chemical Structure| 5317-33-9
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CAS No. :5317-33-9 MDL No. :MFCD00009781
Formula : C8H18N2O Boiling Point : 252.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :158.24 g/mol Pubchem ID :79208
Synonyms :

Safety of [ 5317-33-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5317-33-9 ]

  • Upstream synthesis route of [ 5317-33-9 ]
  • Downstream synthetic route of [ 5317-33-9 ]

[ 5317-33-9 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
86% at 80℃; Intermediate 7: 3-(4-Methylpiperazin-1-yl)-propan-1-ol.
1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL).
3-Bromo-propanol (2.62 mL, 30 mmol) was added slowly and the mixture was stirred overnight.
After heating to 80°C for 2 h and cooling to r.t., the mixture was filtered and the filter cake was washed thoroughly with toluene.
After removal of the toluene, the residue was subjected to Kugelrohr distillation (b.p., 180°C / 2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86 percent).
1H NMR (CDCl3): δ = 1.70 (Ψ-quint, J 5.8 Hz, 2 H), 2.26 (s, 3 H), 2.35-2.6 (m, 8 H), 2.60 (Ψ-t, J = 5.8 Hz, 2 H), 3.77 (Ψ-t, J = 5.3 Hz, 2 H), 4.09 (s, br., 1 H).
86% at 20 - 80℃; Intermediate 9: 3-(4-Methylpiperazin-1-yl)-propan-1-ol.
1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL).
3-Bromopropanol (2.62 mL, 30 mmol) was added slowly and the mixture was stirred overnight at r.t..
After heating to 80°C for 2 h and cooling to r.t., the mixture was filtered and the filter cake was thoroughly washed with toluene.
After removal of the solvent, the residue was subjected to Kugelrohr distillation (b.p., 180°C / 2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86 percent).
1H NMR (CDCl3): δ = 1.70 (Ψ-quint, J 5.8 Hz, 2 H), 2.26 (s, 3 H), 2.35-2.6 (m, 8 H), 2.60 (Ψ-t, J = 5.8 Hz, 2 H), 3.77 (Ψ-t, J 5.3 Hz, 2 H), 4.09 (s, br., 1 H).
86% at 20 - 80℃; Intermediate 9: 3-(4-Methylpiperazin-1-yl)-propan-1-ol
1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL).
3-Bromopropanol (2.62 mL, 30 mmol) was slowly and the mixture was stirred overnight at r.t.
After heating to 80° C. for 2 h and cooling to r.t., the mixture was filtered and the filter cake was thoroughly washed with toluene.
After removal of the solvent, the residue was subjected to distillation (b.p., 180° C./2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86percent).
1H NNR (CDCl3): δ=1.70 (Ψ-quint, J5.8 Hz, 2 H), 2.26 (s, 3 H), 2.35-2.6 (m, 8 H), 2.60 (Ψ-t, J=5.8 Hz, 2 H), 3.77 (Ψ-t, J=5.3 Hz, 2 H), 4.09 (s, br., 1 H).
86% at 80℃; 3-(4-Methylpiperazin-1-yl)-propan-1-ol. 1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromopropanol (2.62 mL, 30 mmol) was added slowly and the mixture was stirred overnight. After heating to 80° C. for 2 h and cooling to r.t., the mixture was filtered and the filter cake was washed thoroughly with toluene. After removal of the toluene, the residue was subjected to Kugelrohr distillation (b.p., 180° C./2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86percent). 1H NMR (CDCl3): δ=1.70 (Ψ-quint, J5.8 Hz, 2H), 2.26 (s, 3H), 2.35-2.6 (m, 8H), 2.60 (Ψ-t, J=5.8 Hz, 2H), 3.77 (Ψ-t, J=5.3 Hz, 2H), 4.09 (s, br., 1H).
86% at 20 - 80℃; Synthesis of 3-(4-methylpiperazin-1-yl)-propan-1-ol: [Show Image] 1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromopropanol (2.62 mL, 30 mmol) was added slowly and the mixture was stirred overnight at r.t.. After heating to 80°C for 2 h and cooling to r.t., the mixture was filtered and the filter cake was thoroughly washed with toluene. After removal of the solvent, the residue was subjected to Kugelrohr distillation (b.p., 180°C / 2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86percent). LC/ESI-MS: m/z = 159 [M+H].

Reference: [1] Patent: EP1674467, 2006, A1, . Location in patent: Page/Page column 26
[2] Patent: EP1674466, 2006, A1, . Location in patent: Page/Page column 27
[3] Patent: US2006/142570, 2006, A1, . Location in patent: Page/Page column 17
[4] Patent: US2006/135782, 2006, A1, . Location in patent: Page/Page column 26
[5] Patent: EP1746096, 2007, A1, . Location in patent: Page/Page column 25
[6] Patent: US2003/199491, 2003, A1,
[7] Patent: US2003/212055, 2003, A1,
[8] Patent: WO2004/41811, 2004, A1, . Location in patent: Page 63
[9] Patent: US2007/21446, 2007, A1, . Location in patent: Page/Page column 14
[10] Patent: US2004/48881, 2004, A1,
[11] Patent: US2004/44015, 2004, A1,
[12] Patent: US2003/225111, 2003, A1, . Location in patent: Page 42
[13] Patent: WO2004/4732, 2004, A1, . Location in patent: Page/Page column 71
[14] Patent: US6806274, 2004, B1, . Location in patent: Page/Page column 71
[15] Patent: WO2004/5284, 2004, A1, . Location in patent: Page 76
  • 2
  • [ 109-01-3 ]
  • [ 627-30-5 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 18, p. 6728 - 6737
  • 3
  • [ 5317-32-8 ]
  • [ 50-00-0 ]
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 6511,6512
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  • [ 55-86-7 ]
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Reference: [1] Patent: GB901187, 1958, ,
  • 5
  • [ 109-01-3 ]
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Reference: [1] Monatshefte fuer Chemie, 1956, vol. 87, p. 701,706
[2] Bulletin de la Societe Chimique de France, 1959, p. 576,578
  • 6
  • [ 33544-40-0 ]
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Reference: [1] Monatshefte fuer Chemie, 1956, vol. 87, p. 701,706
  • 7
  • [ 7148-05-2 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 576,578
  • 8
  • [ 109-01-3 ]
  • [ 107-18-6 ]
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Reference: [1] Patent: GB807750, 1957, ,
  • 9
  • [ 66443-73-0 ]
  • [ 5317-33-9 ]
  • [ 4223-94-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 11-12, p. 565 - 570
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