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

HRID 1262450Notes

Reaction equation

HRID 1262450 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]>[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]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]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 112%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Parr bottle, N,N-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide (2.20 g, 0.0079 mol), 10% Palladium on Carbon (50% Wet)(5:45:50, Palladium:carbon black:Water, 0.84 g, 0.0004 mol) and Methanol (50 mL, 1 mol) were added. The mixture was evacuated and charged with hydrogen at 40 psi. The reaction was shaken on the parr at 40 psi for one hour. The mixture was filtered through Celite and the Celite washed with EtOAc. The organic was evaporated under vacuum to give N,N-Dimethyl-2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide as a brown gum/foam (1.96 g, 112%). LCMS (E/I+) 248 (M+H). NMR 1H (DSMO-d6)-9.90 (br. s, 2H), 7.22 (d, 1H, J=8.14 Hz), 7.06 (m, 2H), 4.36 (s, 2H), 3.66 (br. m, 4H), 3.12 (br. m, 4H), 2.96 (s, 3H), 2.91 (s, 3H).

Workup

  1. customThe mixture was evacuated
  2. additioncharged with hydrogen at 40 psi
  3. filtrationThe mixture was filtered through Celite
  4. washthe Celite washed with EtOAc
  5. customThe organic was evaporated under vacuum

Sources & evidence

ORD record
ord-aaa6c7a3f45d4f85a60543f94b65cd81
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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