(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine → (1S)-8,9-Dichloro-1,3-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 645393Notes

Reaction equation

HRID 645393 reaction equation
ClC1C=CC2CCNC[C@@H](C)C=2C=1Cl.[CH3:15][N:16]1[CH2:22][C@H:21]([CH3:23])[C:20]2[C:24]([Cl:29])=[C:25]([Cl:28])[CH:26]=[CH:27][C:19]=2[CH2:18][CH2:17]1>>[CH3:15][N:16]1[CH2:22][C@@H:21]([CH3:23])[C:20]2[C:24]([Cl:29])=[C:25]([Cl:28])[CH:26]=[CH:27][C:19]=2[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 11608308(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineHCID 59264538(1R)-8,9-Dichloro-1,3-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 59264537(1S)-8,9-Dichloro-1,3-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Procedure

Compound 10 was prepared from (S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243.

Sources & evidence

ORD record
ord-66675701299046169af471e960460f85
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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