Hydrochloric Acid → Benzyl 3-(hydroxymethyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate hydrochloride

HRID 2079325Notes

Reaction equation

HRID 2079325 reaction equation
[ClH:1].CCOCC.[CH2:7]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([CH3:33])=[CH:30][CH:31]=3)[N:26]=[C:25]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[OH:40])[N:24]=2)[CH:19]([CH2:41][OH:42])[CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[ClH:1].[OH:42][CH2:41][CH:19]1[N:20]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([CH3:33])=[CH:30][CH:31]=3)[N:26]=[C:25]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[OH:40])[N:24]=2)[CH2:21][CH2:22][N:17]([C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:16])[CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1361213213-Hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 136366705Benzyl 3-(hydroxymethyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.0 M HCl solution in Et2O (212 μL, 0.42 mmol) was slowly added at room temperature to a stirring solution of 3-hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid benzyl ester (206 mg, 0.42 mmol) in 500 μL of CH2Cl2. The reaction was stirred for 1 hour. Solvents were removed under reduced pressure, and the residue was triturated with Et2O and filtered to give benzyl 3-(hydroxymethyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate hydrochloride. LC/MS: m/z 485.5 (M+H)+ at 3.07 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a0657bce9b4e4d76b0045d197aa00f51
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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