4-Toluenesulfonyl chloride → 1-Chloro-2,2-dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane

HRID 342601Notes

Reaction equation

HRID 342601 reaction equation
[CH3:1][C:2]([CH3:24])([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:8][CH2:7]1)[CH2:3]O.C(N(CC)CC)C.C1(C)C=CC(S([Cl:41])(=O)=O)=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:41][CH2:3][C:2]([CH3:1])([CH3:24])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 702011642,2-Dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-1-propanol

Product 1

HCID 702017211-Chloro-2,2-dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propaneYield 19,705.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2-dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-1-propanol (991 mg, 2.9 mol), triethylamine (0.4 mL, 2.9 mmol), p-toluenesulfonyl chloride (678 mg, 3.4 mmol), 4-dimethylaminopyridine (35 mg, 0.29 mmol) and methylene chloride (15 mL) was stirred 8 hours at 20° to 25° C. The reaction mixture then was filtered and concentrated and the residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (95:5) to give 1-chloro-2,2-dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane (238 mg, 0.67 mol).

Workup

  1. filtrationThe reaction mixture then was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-d4e725bddf2b45f49e91de8c18bd79cc
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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