Lithium Chloride → 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-2-ethyl-butyric acid hydrochloride salt

HRID 229114Notes

Reaction equation

HRID 229114 reaction equation
C[O:2][C:3](=[O:46])[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[C:36]=2[Cl:45])[CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1)([CH2:7][CH3:8])[CH2:5][CH3:6].[Li+].[Cl-]>CN(C=O)C>[ClH:45].[Cl:45][C:36]1[C:37]([C:41]([F:42])([F:43])[F:44])=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][N:19]([CH2:20][CH:21]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:18][CH2:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]([C:4]([CH2:5][CH3:6])([CH2:7][CH3:8])[C:3]([OH:46])=[O:2])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 577571032-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-2-ethyl-butyric acid methyl ester

Product 1

HCID 688622372-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-2-ethyl-butyric acid hydrochloride salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-2-ethyl-butyric acid methyl ester (30 mg, 0.05 mmol) in DMF (9 mL) was treated with LiCl (20 mg, 0.46 mmol). The resulting reaction mixture was heated to reflux overnight and concentrated. The crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A:acetonitrile B:water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give the title compound, the free amine as an oil (15 mg, 45%). To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0 M) to precipitate the amine salt. The suspension was filtered and dried to give the title compound as a white solid. MS m/e 638.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. concentrationconcentrated
  5. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-d795d65e4fe64802a6bd258ecdbc1520
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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