Phenethylamine, m-trifluoromethyl- → (2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

HRID 855217Notes

Reaction equation

[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][NH2:24])[CH:19]=[CH:20][CH:21]=1.[BH4-].[Na+]>>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][NH:24][CH2:23][CH2:22][C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:14])([F:25])[F:26])[CH:17]=3)=[CH:10][C:4]=2[O:3]1

Participants

Reactant 3

HCID 104223Phenethylamine, m-trifluoromethyl-

HCID 27369732,2-Difluoro-5-formylbenzodioxole

HCID 4311764Sodium borohydride

Product 1

HCID 69346679(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Procedure

(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine was synthesized in analogy to the above procedure using 100 mg of 2,2-difluoro-1,3-benzodioxole-5-carbaldehyde (0.54 mmol), 102 mg of 2-(3-trifluoromethylphenyl)-ethylamine (0.54 mmol) and 31 mg of sodium borohydride (0.81 mmol). The isolated colorless semisolid (110 mg, 57%) was used in the following step without further purification. MS (ISP) 360.0 (M+H)+.

Workup

customThe isolated colorless semisolid (110 mg, 57%) was used in the following step without further purification

Sources & evidence

ORD record: ord-ec98f5ee4fde4f3f9b851051c317bcba
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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