Hydrochloric Acid → HCID 46832950, compound

HRID 1622911Notes

Reaction equation

HRID 1622911 reaction equation
Cl.[F:2][C:3]([F:31])([F:30])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:29])[C:17]([C:19]3[CH:28]=[CH:27][C:22]4[NH:23][C:24](=[O:26])[S:25][C:21]=4[CH:20]=3)=[O:18])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[BH4-].[Na+].Cl>CO>[OH:18][CH:17]([C:19]1[CH:28]=[CH:27][C:22]2[NH:23][C:24](=[O:26])[S:25][C:21]=2[CH:20]=1)[CH:16]([N:13]1[CH2:12][CH2:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:2])([F:30])[F:31])[CH:5]=2)[CH2:15][CH2:14]1)[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68000749HCID 68000749, compound

Product 1

HCID 46832950HCID 46832950, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 6-(2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propanoyl)benzo[d]thiazol-2(3H)-one hydrochloride (1.89 g, 4 mmol) was dissolved in 50 ml of methanol solution, and sodium borohydride (0.15 g, 8.4 mmol) was added in proportions, mixed and stirred at room temperature for 3 hours. Working up according to general procedure B gave 0.61 g of (1RS, 2SR)-6-(1-hydroxy-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)benzo[d]thiazol-2(3H)-one (IV-5) hydrochloride having a melting point of 217 to 219° C., with a yield of 32.2%; and 0.57 g of (1RS,2RS)-6-(1-hydroxy-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)benzo[d]thiazol-2(3H)-one (IV-6) hydrochloride having a melting point of 235 to 237° C., with a yield of 30%.

Workup

  1. additionmixed

Sources & evidence

ORD record
ord-2bc9a35803e24a08921e6bdb5005b84d
Source dataset
uspto-grants-2014_07
Patent number
US08778948B2

Reaction notes

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