Water → 4-(Diphenylmethyl)piperazine-1-carbonyl chloride

HRID 251836Notes

Reaction equation

HRID 251836 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:26][C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl.O>ClCCl>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:27]([Cl:26])=[O:29])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 70048BenzhydrylpiperazineHCID 94429Triphosgene

Product 1

HCID 282861154-(Diphenylmethyl)piperazine-1-carbonyl chlorideYield 216%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2.522 g (10 mmol) of 1-benzhydrylpiperazine and of 1.62 ml (20 mmol) of pyridine in 15 ml of dichloromethane is added, dropwise, to a solution of 1.187 g (4 mmol) of triphosgene in 10 ml of dichloromethane, cooled to −5° C. under an argon atmosphere. Stirring is continued at −5° C. for 15 minutes and then at ambient temperature for 3 hours. 50 ml of dichloromethane and 50 ml of water are subsequently added. The mixture is separated by settling out and the organic phase is washed with 2×25 ml of water and then 25 ml of a saturated aqueous solution of sodium chloride. The product is dried over sodium sulfate and evaporated under vacuum, so as to obtain 2.72 g of product in the form of a gum, used as it is in the following step.

Workup

  1. waitat ambient temperature for 3 hours
  2. customThe mixture is separated
  3. washthe organic phase is washed with 2×25 ml of water
  4. dry with materialThe product is dried over sodium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-cef1d89ef31e4c8bb17d4e8ace0b5182
Source dataset
uspto-grants-2011_01
Patent number
US07868007B2

Reaction notes

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