Hydrochloric Acid → 3-Cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one hydrochloride

HRID 2079282Notes

Reaction equation

HRID 2079282 reaction equation
[ClH:1].C(OCC)C.[CH:7]1([CH2:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:31]4[C:26](=[CH:27][C:28]([CH3:32])=[CH:29][CH:30]=4)[N:25]=[C:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[OH:39])[N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1>C(Cl)Cl>[ClH:1].[CH:7]1([CH2:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:31]4[C:26](=[CH:27][C:28]([CH3:32])=[CH:29][CH:30]=4)[N:25]=[C:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[OH:39])[N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 1361214493-Cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one

Product 1

HCID 1363669023-Cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an N2 atmosphere, a 1 M HCl solution in diethyl ether (0.54 mL, 0.54 mmol) was added dropwise to a stirring solution of 3-cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one (240 mg, 0.54 mmol) in CH2Cl2 (20 mL). After 10 min, ether was added until a precipitate formed. The solid was collected by filtration and dried under vacuum to give 3-cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one hydrochloride (230 mg, 88%). LC/MS: m/z 445.30 (M+H)+ at 3.08 min (10%-99% CH3CN (0.035% TFA)4H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) d 8.26 (d, J=8.0 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.78 (s, 1H), 7.50-7.46 (m, 2H), 7.09 (d, J=8.1 Hz, 1H), 7.04-7.00 (m, 1H), 4.15-4.11 (m, 4H), 3.79-3.74 (m, 4H), 2.54 (s, 3H), 2.37 (t, J=7.7 Hz, 2H), 1.82-1.74 (m, 3H), 1.60-1.45 (m, 6H), 1.12-1.08 (m, 2H) ppm.

Workup

  1. customformed
  2. filtrationThe solid was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c3b81bcaf58349489eea1763b19c9415
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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