Hydrochloric Acid → HCID 68932425, compound

HRID 1437523Notes

Reaction equation

HRID 1437523 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH2:8][CH2:7][CH2:6][C:5]2=1.[ClH:24]>CO>[ClH:24].[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C@@H:9]([NH:15][C@@H:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14197120HCID 14197120, compound

Product 1

HCID 68932425HCID 68932425, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(1S)-6-Methyl-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt was prepared by separation of diastereomeric 6-methyl-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazol-1-amine by SFC (Berger Amino, 10% methanol, 1500 psi, 40° C., 2 mL/min, retention time: 10.0 min.) The oil obtained was converted to the HCl salt to give a white solid. [α]25=−20.0 (c 0.20, MeOH); 1H-NMR (DMSO-d6): δ 7.58 (d, J=7.6 Hz, 2H), 7.55-7.46 (m, 3H), 7.26 (d, J=8.0 Hz, 1H), 7.26 (m, 1H), 7.01 (d, J=8.8 Hz, 1H), 4.74 (q, J=7.2 Hz, 1H), 4.43 (t, J=4.8 Hz, 1H), 2.82 (dt, J=16.4 Hz, J=4.0 Hz, 1H), 2.68 (dt, J=16.4 Hz, J=4.8 Hz, 1H), 2.40 (s, 3H), 2.32-2.20 (m, 1H), 2.18-2.00 (m, 2H), 1.98-1.88 (m, 1H), 1.75 (d, J=6.8 Hz, 3H); MS m/z 184 (M−121); Anal. Calcd. For C21H25BrN2Cl: C, 73.99; H, 7.39; N, 8.22. Found: C, 74.02; H, 7.30; N, 8.31.

Workup

  1. customobtained
  2. customto give a white solid

Sources & evidence

ORD record
ord-4bac3bcc6f0c41e5a55858a4a3de1f5c
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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