Sodium Hydroxide → 2-((4-Bromobenzyl)amino)acetamide

HRID 1097242Notes

Reaction equation

HRID 1097242 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[NH2:11][CH2:12][C:13]([NH2:15])=[O:14].[OH-].[Na+].[BH4-].[Na+]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:11][CH2:12][C:13]([NH2:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 707414-BromobenzaldehydeHCID 2723639Glycinamide hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 167779692-((4-Bromobenzyl)amino)acetamideYield 78.8%

Procedure

To a solution of 4-bromobenzaldehyde (100 g, 0.54 mol) and glycinamide hydrochloride (54 g, 0.48 mol) methanol/water (1500 ml, 5.5/1) was added sodium hydroxide (21.6 g, 0.54 mol). After stirring for 17 h at room temperature the reaction mixture was cooled to 0° C. Sodium borohydride (38 g, 1.0 mol) was added and the mixture was stirred until a clear solution was obtained. The reaction was quenched by addition of concentrated hydrochloric acid until pH=3. After stirring for 17 h the mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate and the product was extracted into dichloromethane. The combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure to afford 2-(4-bromobenzylamino)acetamide (92 g).

Workup

  1. temperaturewas cooled to 0° C
  2. stirringthe mixture was stirred until a clear solution
  3. customwas obtained
  4. customThe reaction was quenched by addition of concentrated hydrochloric acid until pH=3
  5. stirringAfter stirring for 17 h the mixture
  6. extractionthe product was extracted into dichloromethane
  7. washThe combined organic phases were washed with water, brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bae6ccf57bf4608b80ba4956c4a961c
Source dataset
uspto-grants-2012_03
Patent number
US08143246B2

Reaction notes

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