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 10086Notes

Reaction equation

HRID 10086 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) δ 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-6dc5260fbcaf4265958a4eac66912ab7
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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