Hydrazine hydrate (1:1) → HCID 67263815, compound

HRID 1040746Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:18]([N+:19]([O-])=O)=[CH:17][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:11][C:5]=2[CH:4]=1.O.NN>CO.[Pd]>[CH3:1][O:2][C:3]1[C:18]([NH2:19])=[CH:17][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]([F:14])([F:15])[F:16])[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-8-nitro-3-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (310 mg, 1.0 mmol), hydrazine monohydrate (10 mL, 0.2 mol), palladium (10% wt on C, 50% wet; 100 mg, 0.9 mmol), in methanol (20 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite and was concentrated. The resulting precipitate was partitioned between water and dichloromethane. The organic phase was washed with another portion of water, dried (MgSO4), and concentrated, to afford 8-methoxy-3-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (245 mg, 88%) as a waxy solid, which was used without further purification. m.p. ° C.; 1H-NMR (CDCl3) δ 6.55 (s, 1H), 6.49 (s, 1H), 3.82 (s, 3H), 3.63 (br s, 2H), 3.15 (q, J=9.5 hz, 2H), 2.88 (m, 4H), 2.77 (m, 4H); LC/MS (ESI+): 275.07 (M+H).

Workup

filtrationThe reaction mixture was filtered through Celite
concentrationwas concentrated
customThe resulting precipitate was partitioned between water and dichloromethane
washThe organic phase was washed with another portion of water
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-b7959c5c21ca4f58a7e58317284a72b3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

Loading…