Thionyl Chloride → HCID 4935532, compound

HRID 2278158

Reaction equation

HRID 2278158 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C(Cl)Cl>[C:21]([N:28]1[CH2:29][CH2:30][N:31]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[CH2:32][CH2:33]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5204294,4'-Dibromobenzhydrol

Product 1

HCID 4935532HCID 4935532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of bis(4-bromophenyl)methanol (0.060 mmol) in CH2Cl2 (0.3 mL) was added thionyl chloride (40 μL, 0.60 mmol) and the reaction mixture was stirred for 48 h. The reaction was evaporated to dryness under a stream of N2 and the crude product redissolved in acetonitrile (1.0 mL). 1-Boc-piperazine (22.3 mg, 0.12 mmol) was added and the reaction mixture was refluxed for 4 h. The reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2 and passed through a short pad of SiO2, providing the 1-Boc-4-diphenylmethylpiperazine.

Workup

  1. customThe reaction was evaporated to dryness under a stream of N2
  2. dissolutionthe crude product redissolved in acetonitrile (1.0 mL)
  3. temperaturethe reaction mixture was refluxed for 4 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionredissolved in CH2Cl2

Sources & evidence

ORD record
ord-ba3e0929aa8e462081f04aea86fa36ba
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Linked notes

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