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

HRID 645389Notes

Reaction equation

HRID 645389 reaction equation
FC(F)(F)C(N1C[C@H](C)C2C=C(Cl)C=CC=2CC1)=O.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]([CH3:31])[C:25]=2[C:32]=1[Cl:33]>>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[CH2:30][CH2:29][NH:28][CH2:27][C@H:26]([CH3:31])[C:25]=2[C:32]=1[Cl:33]

Participants

3

Reactant 2

HCID 11608308(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineHCID 86613109HCID 86613109, compound

Product 1

HCID 24773894(1R)-8,9-Dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Procedure

Compound,7 was prepared from (R)-N-trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar two step procedure as described herein for the preparation of Compound 5. 1H NMR (400 MHz, CDCl3) δ 7:40 (d, J=8 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 4.17 (m, 1H), 3.55 (m, 2H), 3.5-3.3 (m, 2H), 3.2-3.0 (m, 2H), 1.43 (d, J=7 Hz, 3H). MS calculated for C11H13Cl2N+H: 230, observed: 230.

Sources & evidence

ORD record
ord-1aeea046d2b04302ad819d4557d46ebb
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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