Ethanol → Hydrogen Bromide

HRID 2417876Notes

Reaction equation

HRID 2417876 reaction equation
[BrH:1].C([N:9]([CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:27]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[CH:26]=1)=[O:24])[CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.C(O)C>O.[C].[Pd]>[C:39]([O:38][C:27]1[CH:26]=[C:25]([CH:23]([OH:24])[CH2:22][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:30]=[CH:29][C:28]=1[O:31][C:32](=[O:37])[C:33]([CH3:35])([CH3:36])[CH3:34])(=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43].[BrH:1]

Participants

6

Reactant 2

HCID 702EthanolHCID 20446768HCID 20446768, compound

Product 2

HCID 260Hydrogen BromideYield 561.1%HCID 12876234HCID 12876234, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(pivaloyloxy)acetophenone hydrobromide (2.5 g.) in a mixture (50 ml.) containing 70% v/v of ethanol in water was hydrogenated for 18 hours at a pressure of 3.5 kg./cm2 at room temperature using 10% palladium-carbon (0.8 g.). The catalyst was separated by filtration and the filtrate evaporated. Trituration of the residue with ether (30 ml.) containing several drops of ethanol gave 1-[3,4-bis(pivaloyloxy)phenyl]-2-[2-(2-phenylacetamido)ethylamino]ethanol as its hydrobromide (1.7 g.) m.p. 111°-113° C. (hemi-hydrate).

Workup

  1. customat room temperature
  2. customThe catalyst was separated by filtration
  3. customthe filtrate evaporated
  4. additionTrituration of the residue with ether (30 ml.) containing several drops of ethanol

Sources & evidence

ORD record
ord-f556054fa27b48bbb9d1457c34b7eb0a
Source dataset
uspto-grants-1984_09
Patent number
US04470997

Reaction notes

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