Dichloromethane → 1,1,1-Trifluoro-2-(4-(2-(hydroxymethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HRID 1972405Notes

Reaction equation

C([O:8][CH2:9][CH:10]1[CH2:15][N:14]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)C1C=CC=CC=1.C(Cl)Cl.B(Cl)(Cl)Cl>CO>[F:34][C:31]([F:32])([F:33])[C:30]([C:27]1[CH:28]=[CH:29][C:24]([N:11]2[CH2:12][CH2:13][N:14]([S:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:18])[CH2:15][CH:10]2[CH2:9][OH:8])=[CH:25][CH:26]=1)([OH:36])[CH3:35]

Participants

Conditions

Temperature: -78 °C

Procedure

A 250 mL round-bottomed flask was charged with 2-(4-(2-((benzyloxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (2.93 g, 5.43 mmol) and CH2Cl2 (50 mL) and cooled to −78° C. A 1.0 M solution of BCl3 (1M in CH2Cl2, 7.31 mL, 7.31 mmol, Sigma-Aldrich, St. Louis, Mo.) was added slowly to the mixture and the reaction was stirred for 1 h at −78° C. After this time, MeOH (25 mL) was added and the mixture was warmed to room temperature. After the MeOH was removed in vacuo, diethyl ether (100 mL) was added. The resulting precipitate was collected by filtration, dried under reduced pressure to yield 1,1,1-trifluoro-2-(4-(2-(hydroxymethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (2.17 g) as a mixture of four isomers.

Workup

temperaturethe mixture was warmed to room temperature
customAfter the MeOH was removed in vacuo, diethyl ether (100 mL)
additionwas added
filtrationThe resulting precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-295502294cb4443980ae9cdc30f3969a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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