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

HRID 855336

Reaction equation

HRID 855336 reaction equation
C1([C:4]2[CH:24]=[CH:23][C:7]([CH2:8][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15](F)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:6][CH:5]=2)CC1.[CH3:25][C:26]1([CH3:37])[O:30]C2C=CC(C=O)=CC=2[O:27]1.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[CH3:25][C:26]1([CH3:37])[O:30][C:4]2[CH:5]=[CH:6][C:7]([CH2:8][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:13]=3)=[CH:23][C:24]=2[O:27]1

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 5960122,2-Dimethylbenzo[d][1,3]dioxole-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

Product 1

HCID 69346752(2,2-Dimethyl-benzo[1,3]dioxol-5-ylmethyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Procedure

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 84 mg of 2,2-dimethyl-benzo[1,3]dioxole-5-carbaldehyde (0.47 mmol), 89 mg of 2-(3-trifluoromethylphenyl)-ethylamine (0.47 mmol) and 27 mg of sodium borohydride (0.71 mmol). The isolated colorless semisolid (137 mg, 83%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.66 (s, 6H), 2.89 (m, 4H), 3.70 (s, 2H), 6.68 (m, 3H), 7.39 (m, 2H), 7.46 (m, 2H).

Workup

  1. customThe isolated colorless semisolid (137 mg, 83%) was used in the following step without further purification

Sources & evidence

ORD record
ord-5d64cc06e90243dbb7bde481d6e2fa1f
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Linked notes

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