Hydrochloric Acid → HCID 11154297, compound

HRID 1437512Notes

Reaction equation

HRID 1437512 reaction equation
[Br: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][CH:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[CH2:8][CH2:7][CH2:6][C:5]2=1.[ClH:25]>CO>[ClH:25].[Br: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][CH:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44583636HCID 44583636, compound

Product 1

HCID 11154297HCID 11154297, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R)-6-Bromo-N-(2,3-dihydro-1H-inden-2-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt was prepared by separation of racemic 6-bromo-N-(2,3-dihydro-1H-inden-2-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine by Super critical Fluid Chromatography (hereinafter “SFC”) (Diacel AD-H, Chiral Technologies, 30% methanol, 3000 psi, 40° C., 2 mL/min, retention time: 16.6 min.) The oil obtained was converted to the HCl salt to give a white solid. 1H-NMR (DMSO-d6): δ 11.4 (s, 1H), 9.61 (s, 1H), 9.42 (s, 1H), 7.69 (s, 1H), 7.36 (d, 1H), 7.35-7.19 (m, 5H), 4.68 (t, 1H), 4.32 (m, 1H), 3.47 (dd, 1H), 3.32 (m, 3H), 2.74 (m, 1H), 2.65 (m, 1H), 2.18 (m, 2H), 2.01 (m, 1H), 1.87 (m, 1H); MS m/z 379, 381 (ES-1).

Workup

  1. customobtained
  2. customto give a white solid

Sources & evidence

ORD record
ord-ce6c1ce9a9034b0e946dca61e1537ffa
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

Loading…