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

HRID 1891253Notes

Reaction equation

HRID 1891253 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[K+].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O.C(Cl)Cl.[Cl-].[Na+]>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:2][CH2:3][C:4]([NH2:6])=[O:5])=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 707414-BromobenzaldehydeHCID 2723639Glycinamide hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 167779692-((4-Bromobenzyl)amino)acetamideYield 58.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To glycinamide hydrochloride (1B2) (129 mmol, 15.4 g) in methanol (343 ml) was added potassium hydroxide (9.27 mmol, 0.520 g) followed by 4-bromobenzaldehyde (1B1) (93 mmol, 17.15 g) and the mixture stirred for 15 minutes at 0° C. Sodium triacetoxyborohydride (278 mmol, 58.9 g) was added and stirring continued for 1 h. The reaction was diluted with water (75 ml), DCM (300 ml) and saturated sodium chloride solution (100 ml) and the phases separated. The aqueous layer was washed twice with DCM (100 ml) before addition of sodium hydroxide solution to ˜pH10 and the resulting precipitate was collected by filtration to give 2-(4-bromobenzylamino)acetamide (1B3) 13.2 g (58.5%); 1H NMR (400 MHz, DMSOd6) δ 7.50 (d, 2H) 7.31 (d, 2H) 7.08 (bs, NH2) 3.65 (s, 2H) 3.01 (s, 2H) 2.58 (bs, NH).

Workup

  1. stirringstirring
  2. waitcontinued for 1 h
  3. customthe phases separated
  4. washThe aqueous layer was washed twice with DCM (100 ml) before addition of sodium hydroxide solution to ˜pH10
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e57cbca16f5145e989fd20c12b14b46f
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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