7-nitro-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine → 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-1,5-methano3-benzazepin-7-amine

HRID 457424Notes

Reaction equation

HRID 457424 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]2[CH:11]3[CH2:15][CH:7]([CH2:8][N:9]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:10]3)[C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:12]2[CH:11]3[CH2:15][CH:7]([CH2:8][N:9]([C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])[CH2:10]3)[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 218647057-nitro-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine

Product 1

HCID 218647163-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-1,5-methano3-benzazepin-7-amineYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogenation of 1-(4-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (2.0 g, 6.66 mmol) under a hydrogen atmosphere (40 psi, or approximately 2.7 atmospheres) and 10% Pd/C (200 mg) in methanol over 1.5 hours, filtration through Celite and concentration affords a yellow oil (1.7 g). (TLC 50% ethyl acetate/hexanes Rf 0.27). 1H NMR (400 MHz, CDCl3)6.99 (m, 1H), 6.64 (br s, 1H), 6.57 (m, 1H), 4.25 (m, 1H), 3.82 (m, 1H), 3.50 (m, 1H), 3.17–3.07 (m, 3H), 2.35 (m, 1H), 1.90 (d, J=10.8 Hz, 1H). GCMS m/e 270 (M+).

Workup

  1. filtrationfiltration
  2. concentrationthrough Celite and concentration

Sources & evidence

ORD record
ord-a880c0b1b48f40f4af27ea392fc22e4b
Source dataset
uspto-grants-2007_03
Patent number
US07186870B2

Reaction notes

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