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[ CAS No. 83101-12-6 ]

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2D
Chemical Structure| 83101-12-6
Chemical Structure| 83101-12-6
Structure of 83101-12-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 83101-12-6 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 83101-12-6 ]

SDS

Product Details of [ 83101-12-6 ]

CAS No. :83101-12-6MDL No. :MFCD09028771
Formula :C10H11NOBoiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :161.20Pubchem ID :11084178
Synonyms :

Computed Properties of [ 83101-12-6 ]

TPSA : 44 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.30 Rotatable Bond Count : 3

Safety of [ 83101-12-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H227-H302+H312+H332-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83101-12-6 ]

  • Upstream synthesis route of [ 83101-12-6 ]
  • Downstream synthetic route of [ 83101-12-6 ]

[ 83101-12-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 80151-16-2 ]
  • [ 83101-12-6 ]
Reference: [1] Patent: WO2004/54584, 2004, A1. Location in patent: Page/Page column 24
[2] Patent: WO2004/83173, 2004, A2. Location in patent: Page 29
[3] Patent: US2005/20591, 2005, A1. Location in patent: Page/Page column 14
[4] Patent: EP2168944, 2010, A1. Location in patent: Page/Page column 150
  • 2
  • [ 20655-58-7 ]
  • [ 83101-12-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 115 - 126
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6638 - 6646
[3] Patent: US2008/312191, 2008, A1. Location in patent: Page/Page column 31
[4] Patent: WO2007/45496, 2007, A1. Location in patent: Page/Page column 68-70; 75-76
  • 3
  • [ 42287-94-5 ]
  • [ 83101-12-6 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In tetrahydrofuran; water 4)
Synthesis of 3-(4-Cyanophenyl)propanol Borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 33.0 ml, 33.0 mmol) was added dropwise to a stirred solution of 3-(4-cyanophenyl)propionic acid (4.40 g, 25.1 mmol) in tetrahydrofuran (50 ml) at O{umlaut over (uA)} and the stirring was continued at room temperature for 14 hours.
Water (50 ml) and potassium carbonate (10.0 g, 72.4 mmol) was added to the mixture.
The mixture was extracted with ethyl acetate and the extract was washed with brine, dried over MgSO4 and concentrated in vacuo to give 3-(4-cyanophenyl)propanol as a yellow oil (3.20 g, 79percent).
1H-NMR (200 MHz, CDCl3) δ: 7.58 (2H, d, J=8.2 Hz), 7.31 (2H, d, J=8.2 Hz), 3.68 (2H, t, J=6.2 Hz), 2.79 (2H, t, J=7.8 Hz), 2.00-1.75 (2H, m).
IR (neat): 3319, 2943, 2229, 1608, 1505, 1415, 1054, 854, 817 cm-1.
Reference: [1] Patent: US6235731, 2001, B1
  • 4
  • [ 116460-89-0 ]
  • [ 83101-12-6 ]
YieldReaction ConditionsOperation in experiment
42%
Stage #1: With methanol; lithium borohydride In diethyl ether for 3.00 h; Heating / reflux
Stage #2: With ammonium chloride In diethyl ether; water
To a solution of LiBH4 (14 g, 0.65 mol) in dry ether (400 mL) was added 3- (4-cyanophenyl) propionic acid ethyl ester (50 g, 0.249 mol; see step (ii) above), followed by methanol (27 mL) dropwise. The reaction mixture was refluxed for 3h. After completion (monitored by TLC), the reaction was quenched by adding cold, saturated ammonium chloride solution (100 mL), followed by water (300 mL). The layers were then separated. The aqueous layer was extracted with ether (2 x 100 mL) and the combined organic layers were washed with brine. After drying over anhydrous sodium sulfate, the organic layer was concentrated to give the crude product. This crude product was purified by column chromatography over silica gel, using ethyl acetate in petroleum ether as eluent. This yielded 16.5 g (42percent) of the sub- title compound as a pale yellow liquid.
Reference: [1] Patent: WO2005/123747, 2005, A1. Location in patent: Page/Page column 53
  • 5
  • [ 25574-11-2 ]
  • [ 109-89-7 ]
  • [ 83101-12-6 ]
YieldReaction ConditionsOperation in experiment
52% With 1-methyl-pyrrolidin-2-one In water 33B 3-(4-Cyanophenyl)propan-1-ol
A mixture of 3-(4-bromophenyl)propan-1-ol (2.0 g, 9.3 mmol), copper (I) cyanide (1.49 g, 16.7 mmol) and N-methylpyrrolidinone (13 ml) was stirred at 200°C for 2.5 hours.
After that the reaction mixture was cooled at room temperature, poured onto a solution of diethylamine (30 g) and water (80 ml) and extracted with ethyl acetate (3x40 ml).
The combined organic phases were dried and volatiles were removed, to obtain an oil from which N-methylpyrrolidinone was removed by distillation under high vacuum (0.5 torr, 85°C), thereby obtaining 0.78 g of the title compound (52percent yield).
1H N.M.R. (300 MHz, CDCL3) δ ppm: 1.85 (m, 2H); 2.42 (s broad, 1H); 2.76 (t, 2H); 3.64 (t, 2H); 7.29 (d, 2H); 7.53 (d, 2H).
Reference: [1] Patent: EP775133, 2001, B1
  • 6
  • [ 97190-62-0 ]
  • [ 83101-12-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 25, p. 5492 - 5505
  • 7
  • [ 75567-85-0 ]
  • [ 105-07-7 ]
  • [ 21204-67-1 ]
  • [ 83101-12-6 ]
Reference: [1] Patent: US4987132, 1991, A
  • 8
  • [ 80151-16-2 ]
  • [ 83101-12-6 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 12, p. 2175 - 2179
  • 9
  • [ 16642-94-7 ]
  • [ 83101-12-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 25, p. 5492 - 5505
  • 10
  • [ 35271-56-8 ]
  • [ 83101-12-6 ]
Reference: [1] Pharmazie, 1982, vol. 37, # 3, p. 178 - 182
  • 11
  • [ 1734-79-8 ]
  • [ 83101-12-6 ]
Reference: [1] Pharmazie, 1982, vol. 37, # 3, p. 178 - 182
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