Water → HCID 87158546, compound

HRID 2206900Notes

Reaction equation

HRID 2206900 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[CH2:12]2)=[CH:7][C:6]=1[Br:29])=[N+]=[N-].C1(C)C=CC=CC=1.CP(C)C.O>O1CCCC1>[Br:29][C:6]1[CH:7]=[C:8]([N:11]2[CH2:15][CH2:14][C:13]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:18])([F:17])[F:19])[CH2:12]2)[CH:9]=[CH:10][C:5]=1[CH2:4][NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 68983TrimethylphosphineHCID 89963573HCID 89963573, compound

Product 1

HCID 87158546HCID 87158546, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(Azidomethyl)-3-bromophenyl]-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidine (0.634 g) was dissolved in tetrahydrofuran (10 ml), to the solution was added a 1 M toluene solution (1.37 ml) of trimethylphosphine, and stirred for 10 minutes. To the reaction solution, water (0.09 ml) was added and stirred overnight at room temperature. The volatile compound was distilled off under reduced pressure to obtain almost pure 1-{2-bromo-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methanamine (0.520 g).

Workup

  1. stirringstirred overnight at room temperature
  2. distillationThe volatile compound was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b7a46e64e15647c4bb343ca5ae88107d
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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