Sodium Hydroxide → 2-(3-(3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-3-yl-propyl)-amino]-propoxy}-phenyl)-ethanol Hydrochloride Salt

HRID 902680Notes

Reaction equation

HRID 902680 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:26]=2[Cl:35])[CH2:16][CH:17]([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[CH3:18])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[ClH:35].[Cl:35][C:26]1[C:27]([C:31]([F:34])([F:32])[F:33])=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:15]([CH2:16][CH:17]([C:19]1[CH:23]=[CH:22][S:21][CH:20]=1)[CH3:18])[CH2:14][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69254958HCID 69254958, compound

Product 1

HCID 692532432-(3-(3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-3-yl-propyl)-amino]-propoxy}-phenyl)-ethanol Hydrochloride SaltYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-3-yl-propyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (50 mg, 0.1 mmol) in THF (20 ml) was added LiAlH4 (0.2 ml, 11.0M in diethyl ether). After the reaction mixture was heated to reflux for 4 h it was cooled down to room temperature followed by the addition of NaOH (1 ml, 2N) to quench the reaction. The reaction mixture was filtered and the filtrate was 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 free amine of the title compound as an oil (25 mg, 40%). MS m/e 512.2 (M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M) to precipitate the HCl salt The suspension was filtered and dried to give the title compound as a white solid.

Workup

  1. temperatureAfter the reaction mixture was heated
  2. temperatureto reflux for 4 h it
  3. customto quench
  4. customthe reaction
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-7184af330cef40bc888bd262b659e2a1
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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