Methanol → 3-(2-fluoro-1-fluoromethyl-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

HRID 1687753Notes

Reaction equation

HRID 1687753 reaction equation
[F:1][CH2:2][CH:3]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([O:20][CH3:21])[C:15]([N+:17]([O-])=O)=[CH:16][C:9]=2[CH2:8][CH2:7]1)[CH2:4][F:5].CO>[Pd]>[F:5][CH2:4][CH:3]([N:6]1[CH2:7][CH2:8][C:9]2[CH:16]=[C:15]([NH2:17])[C:14]([O:20][CH3:21])=[CH:13][C:10]=2[CH2:11][CH2:12]1)[CH2:2][F:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 672633093-(2-fluoro-1-fluoromethyl-ethyl)-7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 672643293-(2-fluoro-1-fluoromethyl-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamineYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(2-Fluoro-1-fluoromethyl-ethyl)-7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (670 mg, 2.23 mmol) was dissolved in methanol (40.0 mL, 987 mmol) and 10% Palladium on Carbon (50% Wet) (5:45:50, Palladium:carbon black:Water, 240 mg) was added. The reaction was hydrogenated at 35 psi. for 1 hour. The reaction was filtered through Celite and concentrated under reduced pressure to obtain 3-(2-fluoro-1-fluoromethyl-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine as a green oil (603 mg, 100%). LCMS (m/e) 271 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 6.58 (s, 1H), 6.51 (s, 1H), 4.75-4.66 (m, 2H), 4.64-4.54 (m, 2H), 3.84 (s, 3H), 3.67 (bs, 2H), 3.27-3.09 (m, 1H), 2.90-2.75 (m, 8H).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6be60757ef64c29bcaff83b75b7a107
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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