2,3,4,5-tetrahydro-1H-1-benzazepine → HCID 86691985, compound

HRID 1505718Notes

Reaction equation

HRID 1505718 reaction equation
C(O[C:4]1([C:15]([F:18])([F:17])[F:16])[CH:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5]1)C.FC(F)(F)[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)N[CH:22]=1.[NH:32]1CCCC[C:34]2C=CC=C[C:33]1=2>FC(F)(F)C(O)C(F)(F)F>[CH2:22]([CH:6]1[C:4]([C:15]([F:16])([F:17])[F:18])([OH:5])[N:32]2[C:10]3[CH:9]([CH2:14][CH2:13][CH2:12][C:11]=3[CH:34]=[CH:33]2)[CH2:8][CH2:7]1)[CH2:21][C:29]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 131528853-(Trifluoromethyl)-1H-indoleHCID 15651912HCID 15651912, compound

Product 1

HCID 86691985HCID 86691985, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent2×

Procedure

A solution of 2-ethoxy-3-phenethyl-2-(trifluoromethyl)oxirane (300 mg, 1.15 mmol; prepared as described in RODRIGUES, I., et al., “1-Trifluoromethyl Epoxy Ethers. Effect of Hexafluoro-2-propanol on Reactions with Secondary Aromatic Amines: Synthesis of 3-Trifluoromethyl Indole Derivatives”, J. Org. Chem., 2001, pp 2098-2103, Vol. 66, Issue 6) and 2,3,4,5-tetrahydro-1H-benzo[b]azepine (170 mg, 1.15 mmol) in hexafluoroisopropanol was stirred at room temperature for 48 h. The solvent was evaporated to yield 2-phenethyl-1-(trifluoromethyl)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indol-1-ol (150 mg, 36%) as a diastereomeric mixture, that was used in the next step without further purification.

Workup

  1. customprepared
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0c996e788d754dc8bf7dc813904e09bd
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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