Home Cart 0 Sign in  

[ CAS No. 82752-99-6 ]

{[proInfo.proName]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 82752-99-6
Chemical Structure| 82752-99-6
Structure of 82752-99-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 82752-99-6 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 82752-99-6 ]

SDS

Product Details of [ 82752-99-6 ]

CAS No. :82752-99-6MDL No. :MFCD00935760
Formula :C25H33Cl2N5O2Boiling Point :599.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :506.47Pubchem ID :54911
Synonyms :

Computed Properties of [ 82752-99-6 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 82752-99-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H317-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 82752-99-6 ]

  • Upstream synthesis route of [ 82752-99-6 ]

[ 82752-99-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 115-80-0 ]
  • [ 82752-99-6 ]
YieldReaction ConditionsOperation in experiment
99.5% With hydrogenchloride In isopropyl alcohol; toluene EXAMPLE 9
2[3-[4-(3-Chlorophenyl)-1-piperazinyl]-propyl]-5-ethyl-4-(2-phenoxyethyl-2H-1,2,4-triazol-3(4H)-one monohydrochloride
(Nefazodone monohydrochloride)
2-[3-(4-[3-chlorophenyl]-1-piperazinyl)propyl]-4-(2-phenoxyethyl)-semicarbazide dihydrochloride (23.3 g, 46 mmol) is suspended in 50 ml toluene and refluxing with Dean-Stark apparatus to remove water.
The mixture is then cooled to room temperature and triethyl orthopropionate (50 ml, about 5 eq) is added.
The suspension is refluxed again with Dean-Stark apparatus.
As toluene is distilled the suspension becomes a clear solution which is refluxed for 48 hours.
Distillation under reduced pressure removes unreacted trietyl orthopropionate and the resulting residue is dissolved in 50 ml isopropanol, treated with HCl to pH4, stirred at 0° C. for 1 hour and standed in refrigerator for 12 hours.
The solid is collected with filtration and recrystallized from ethanol to give 10.5 g (45percent) of nefazodone monohydrochloride as white powder (95percent pure by HPLC).
Further purification is achieved by fractional recrystallization to give the product with 99.5percent purity. mp 183-185° C.
IR (KBr) cm-1: 2430-2800 (NH+), 1699 (C=O), 1450-1600 (aromitic); 1 H nmr (CDCl3) δ: 12.39 (s, 1H, HCl), 7.24-7.29 (m, 2H, phenyl H), 7.21 (t, 1H, J=8.0 Hz, phenyl H), 6.91-6.96 (m, 2H, phenyl H), 6.84-6.89 (m, 3H, phenyl H), 6.75 (dd, 1H, J=2.2, 8.3 Hz, phenyl H), 4.19 (t, 2H, J=5.0 Hz, CH2), 4.01 (t, 2H, J=5.0 Hz, CH2), 3.86 (t, 2H, J=6.3 Hz, CH2, 2.96-3.07 (m, 2H, CH2), 3.54-3.70 (m, 6H, 3CH2), 3.09-3.16 (m, 2H, CH2), 2.70(q, 2H, J=7.5 Hz, CH2 C=C), 2.32-2.42 (m, 2H, CH2), 1.31 (t, 3H, J=7.5 Hz, CH3); 13 C nmr (DMSO-d6) δ: 156.8, 152.5, 149.4, 147.2, 133.7, 129.2, 128.4(2C), 120.1, 119.5, 115.4, 113.5, 113.1(2C), 63.9, 53.4, 50.1, 44.6, 41.1, 40.0, 22.0, 17.9, 8.7; elemental analysis for C25 H32 ClN5 O2. HCl: calculated 59.38percent C, 6.58percent H, 13.86percent N; found 59.26percent C, 7.25percent H, 13.61percent N.
Reference: [1] Patent: US5900485, 1999, A
  • 2
  • [ 95885-13-5 ]
  • [ 52605-52-4 ]
  • [ 82752-99-6 ]
YieldReaction ConditionsOperation in experiment
62.5% With hydrogenchloride; sodium hydroxide In dichloromethane; isopropyl alcohol EXAMPLE 6
2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one (Ia) STR28
Reaction in Isopropanol with Sodium Hydroxide. A mixture of 5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one (60.0 g., 0.257 mole), 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine hydrochloride (79.7 g., 0.257 mole), sodium hydroxide (26.7 g., 0.669 mole) and 400 ml. of isopropanol is stirred and heated at reflux for a period of 10 to 18 hrs.
The mixture is acidified with 35 ml. (0.42 mole) of 37percent hydrochloric acid and the solvent concentrated under reduced pressure.
Residual material is stirred with 400 ml. of methylene chloride, filtered, and the filtrate concentrated under reduced pressure.
Crystallization of the residue from 600 ml. of isopropanol affords 81.5 g. (62.5percent yield) of product which is further crystallized from water and then isopropanol to provide 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride, m.p. 180°- 182.5° C.
Spectral (NMR, 13 C NMR, IR) and elemental analysis data are consistent and in accord with that obtained for the identical product of Example 2.
Reference: [1] Patent: US4487773, 1984, A
Historical Records