Water → (+)-4-(1,1-dimethyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)morpholine, tartrate salt

HRID 2421486Notes

Reaction equation

HRID 2421486 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14]N[C:9]=3[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:18]([OH:27])(=[O:26])[C@@H:19]([C@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20].O>CO>[C:23]([CH:21]([CH:19]([C:18]([OH:27])=[O:26])[OH:20])[OH:22])([OH:25])=[O:24].[CH3:8][C:7]1([CH3:17])[C:9]2[CH:8]=[C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:17]=[CH:16][C:10]=2[CH:11]([C:12]2[CH:23]=[CH:21][CH:19]=[CH:14][CH:13]=2)[CH2:3][CH2:2][NH:1]1

Participants

5

Reactant 3

HCID 962WaterHCID 444305L-Tartaric acidHCID 669638998-Morpholinobenzazepine

Product 1

HCID 131728951(+)-4-(1,1-dimethyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)morpholine, tartrate saltYield 166.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the (−)-8-morpholinylbenzazepine (20 mg, 0.058 mmol) form step H above in methanol (1 mL) was added L-tartaric acid (8.6 mg, 0.058 mmol). After the mixture was stirred at room temperature for 10 minutes, water (20 mL) was added. The resulting solution was lyophilized overnight to give (−)-4-(1,1-dimethyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)morpholine, tartrate salt (23.5 mg, 91%, AUC HPLC >99%) as an white solid: 1H NMR (CD3OD, 500 MHz) δ 7.42-7.24 (m, 5H), 7.07 (s, 1H), 6.74 (d, J=8.7 Hz, 1H), 6.56 (d, J=8.7 Hz, 1H), 4.56 (d, J=10.9 Hz, 1H), 4.39 (s, 2H), 3.81 (t, J=4.7 Hz, 4H), 3.63 (br, 1H), 3.35 (br, 1H), 3.31 (s, 3H), 3.11 (t, J=4.7 Hz, 4H), 2.45 (br, 1H), 2.35 (br, 1H), 1.89 (s, 3H), 1.85 (s, 3H); ESI MS m/z 337 [M+H]+.

Workup

  1. waitThe resulting solution was lyophilized overnight

Sources & evidence

ORD record
ord-0eb0b0699d364133a0123ddf36413e3d
Source dataset
uspto-grants-2011_06
Patent number
US07956050B2

Reaction notes

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