Hydrochloric Acid → HCID 68578023, compound

HRID 273009Notes

Reaction equation

HRID 273009 reaction equation
C([N:14]1[CH2:17][CH:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3([CH2:32][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH:14]1[CH2:15][CH:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3([CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68575907HCID 68575907, compound

Product 1

HCID 68578023HCID 68578023, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-{[4-(4-{[1-(benzhydryl)azetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}-morpholine (1.0 g, 1.95 mmol) in ethanol (10 mL) was hydrogenated for 16 hours at room temperature at 60 psi in the presence of Pd(OH)2/C (150 mg, 15% w/w). 2N Hydrochloric acid (few drops) was added and the reaction mixture hydrogenated for 16 hours at 60° C. at 60 psi. The reaction mixture was basified with aqueous sodium carbonate and the mixture filtered over Arbocel® and rinsed with ethanol. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 to 90:10:1 by volume) to provide the title compound (210 mg, 31%). HRMS ESI+ m/z 347.2323 [MH]+.

Workup

  1. filtrationthe mixture filtered over Arbocel®
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 to 90:10:1 by volume)

Sources & evidence

ORD record
ord-35e7536d7c5649258dbddca120f11e6c
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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