Methanol → piperazine-1-carbothioic acid S-[4-(4-fluoro-benzyloxy)-benzyl]ester hydrochloride

HRID 1794069Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.CO.[ClH:35].CCOCC>>[ClH:35].[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([CH2:17][S:16][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:15])=[CH:19][CH:20]=2)=[CH:31][CH:30]=1

Participants

Reactant 3

HCID 887Methanol

HCID 10953452Ether hydrochloride

HCID 86585992HCID 86585992, compound

Product 1

HCID 86585993piperazine-1-carbothioic acid S-[4-(4-fluoro-benzyloxy)-benzyl]ester hydrochloride

Procedure

A solution of 4.89 g (10.6 mmol) 4-[4-(4-fluoro-benzyloxy)-benzylsulfanylcarbonyl]-piperazine-1-carboxylic acid tert-butyl ester in 120.6 ml 1.5M HCl/Et2O and 24.1 ml abs. MeOH was stirred at rt for 6 h. Evaporation of the reaction mixture provided 3.96 g piperazine-1-carbothioic acid S-[4-(4-fluoro-benzyloxy)-benzyl] ester hydrochloride as colourless powder, mp. 169–169.5° C. 1H-NMR(d6-DMSO): 3.05 m, 4H and 3.58–3.75 m, 4H; 4.09 s, 2H; 5.06 s, 2H; 6.94 d, 2H, 7.17–7.30 m, 4H and 7.43–7.55 m, 2H; 9.2 br, 2H. MS (ISP): 361.2 (M+H)+.

Workup

customEvaporation of the reaction mixture

Sources & evidence

ORD record: ord-7a07605bc75c4bf9a37b8f563c41865b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022707B2

Reaction notes

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