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Methanol → [1-(2-Phenylethylsulfonyl)piperidin-4-yl]methanamine

HRID 854302
Notes
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Reaction equation

HRID 854302 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:20])=[O:19])[CH2:14][CH2:13]1)C1C=CC=CC=1.CO.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[C:23]1([CH2:22][CH2:21][S:18]([N:15]2[CH2:14][CH2:13][CH:12]([CH2:11][NH2:10])[CH2:17][CH2:16]2)(=[O:19])=[O:20])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 69413281[1-(2-Phenyl-ethenesulfonyl)-piperidin-4-ylmethyl]-carbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 22135729[1-(2-Phenylethylsulfonyl)piperidin-4-yl]methanamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 2.5 g of [1-(2-phenyl-ethenesulfonyl)-piperidin-4-ylmethyl]-carbamic acid benzyl ester, 1 g of 20% palladium hydroxide on carbon, 200 mL of methanol and 50 mL of tetrahydrofuran were shaken under 50 psi of hydrogen for 2 days at rt. The catalyst was filtered off and washed with 250 mL of methanol. Concentration under reduced pressure gave the C-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-yl]-methylamine as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with 250 mL of methanol
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-4feb9a2adc2146a39f0d570d549a833e
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259157B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes