Hydrazine hydrate (1:1) → 8-Methoxy-3-(2-methoxyethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine

HRID 1687050Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:17]([N+:18]([O-])=O)=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1.O.NN>[Pd].CO>[CH3:1][O:2][C:3]1[C:17]([NH2:18])=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 1-neck round-bottom flask was added 7-methoxy-3-(2-methoxy-ethyl)-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.4 g, 8.56 mmol), hydrazine monohydrate (20 mL, 0.4 mol), and palladium on carbon (10% wt, 50% wet; 400 mg), in methanol (80 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite and was concentrated. The residue was partitioned between diluted NaHCO3 and ethyl acetate. The aqueous phase was extracted with another portion of ethyl acetate, dried (MgSO4), and concentrated to afford 8-methoxy-3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (2.00 g, 93%). 1H-NMR (CDCl3) δ 6.55 (s, 1H), 6.49 (s, 1H), 3.81 (s, 3H), 3.63 (br s, 2H), 3.53 (t, J=5.8 Hz, 2H), 3.36 (s, 3H), 2.60-2.90 (m, 10H); LC/MS (ESI+): 251.10 (M+H).

Workup

filtrationThe reaction mixture was filtered through Celite
concentrationwas concentrated
customThe residue was partitioned between diluted NaHCO3 and ethyl acetate
extractionThe aqueous phase was extracted with another portion of ethyl acetate
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-cd8e0efd09ac42499327faeab1a9524c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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