Isopropanol → HCID 20338498, compound

HRID 1439614Notes

Reaction equation

HRID 1439614 reaction equation
Cl.O[CH:3]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][N:4]1[CH2:15][CH2:16][NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:22])=[O:21].C([OH:30])(C)C>CO.[Pd]>[OH:30][C:7]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][N:4]([CH2:15][CH2:16][NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([NH2:22])=[O:21])[CH2:3][CH2:8]1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 21395746HCID 21395746, compound

Product 1

HCID 20338498HCID 20338498, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[-(2-[Hydroxy-4-phenylpiperidyl]ethyl)amino]benzamide hydrochloride (12 g.) in 200 ml methanol was hydrogenated at 60 psi using 1.5 g 5% Pd-C catalyst (1.5 g and 1.0 g portions of fresh catalyst were added during the reduction). The catalyst was filtered off and the filtrate concentrated to dryness on the rotovap. The residue was recrystallized from 60 ml isopropanol and then from 300 ml isopropanol to give 6.1 product, m.108-13°. Analysis showed 13.39% isopropanol in the product.

Workup

  1. additionwere added during the reduction)
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate concentrated to dryness on the rotovap
  4. customThe residue was recrystallized from 60 ml isopropanol
  5. customfrom 300 ml isopropanol to give 6.1 product, m
  6. custom108-13°

Sources & evidence

ORD record
ord-85f6a11f83f547158ec0816a43087913
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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