Methanol → 2-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamide

HRID 1041379Notes

Reaction equation

HRID 1041379 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.CO>[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:8]2[CH2:7][CH2:6][N:5]([CH2:4][C:3]([N:2]([CH3:1])[CH3:20])=[O:19])[CH2:11][CH2:10][C:9]=2[CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 57416161n,n-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)acetamide

Product 1

HCID 574161402-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N,N-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide (150 mg, 0.541 mmol) was placed in methanol (10.0 mL, 247 mmol) and 10% palladium on carbon (50% Wet) (5:45:50, palladium:carbon black:water, 15.0 mg) was added. The reaction was hydrogenated at 30 psi. for 1 hour, filtered through Celite, and then concentrated under reduced pressure to obtain 2-(7-Amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide as an orange solid (134 mg, 100%). LCMS (m/e) 248 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 6.88 (d, 1H, J=7.5 Hz), 6.50-6.44 (m, 2H), 3.54 (bs, 2H), 3.28 (s, 2H), 3.16 (s, 3H), 2.98 (s, 3H), 2.870-2.81 (m, 4H), 2.71-2.62 (m, 4H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74bc7e9ca4834e5381e7dee315058730
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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