HCID 66965003, compound → 1H-1-Benzazepine

HRID 1478672Notes

Reaction equation

HRID 1478672 reaction equation
C[N:2]1[CH2:8][CH:7]=[C:6](C2C=CC(C)=CC=2)[C:5]2[CH:16]=[CH:17][C:18](N3CCN(C4N=CC=CN=4)CC3)=[CH:19][C:4]=2[CH2:3]1>C(O)C.[OH-].[Pd+2].[OH-]>[NH:2]1[C:3]2[CH:4]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:5]=[CH:6][CH:7]=[CH:8]1

Participants

4

Reactant 1

HCID 66965003HCID 66965003, compound

Product 1

HCID 155596581H-1-BenzazepineYield 121.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the dihydrobenzazepine (0.20 g, 0.49 mmol) from step I above in ethanol (30 mL) was added palladium(II) hydroxide (0.20 g, 0.28 mmol). The reaction solution was shaken under hydrogen (35 psi) for 1 h. The resultant reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by preparative HPLC to give the desired racemic benzazepine (85 mg, 42%) as an off-white foam: 1H NMR (CDCl3, 500 MHz) δ 8.33 (d, J=5.0 Hz, 2H), 7.15 (d, J=8.0 Hz, 2H), 7.06 (d, J=8.0 Hz, 2H), 6.81 (d, J=2.5 Hz, 1H), 6.65 (d, J=7.5 Hz, 1H), 6.62-6.53 (br, 1H), 6.51 (t, J=5.0 Hz, 1H), 4.21 (d, J=9.0 Hz, 1H), 3.96 (t, J=5.0 Hz, 4H), 3.89 (br d, J=12.5 Hz, 1H), 3.70 (d, J=14.0 Hz, 1H), 3.20 (t, J=5.5 Hz, 4H), 3.15-3.08 (br, 1H), 2.93 (t, J=10.5 Hz, 1H), 2.36 (s, 3H), 2.35 (s, 3H), 2.32-2.25 (m, 1H), 2.12-2.04 (br, 1H); ESI MS m/z 414 [M+H]+.

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas filtered through a pad of Celite
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f9fd98e009e04e0ea9d28bd8cc6b0996
Source dataset
uspto-grants-2016_08
Patent number
US09403776B2

Reaction notes

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