Acetic Acid → ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

HRID 355754Notes

Reaction equation

HRID 355754 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][CH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 436161Ethyl 4-(aminomethyl)benzoateHCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22675503ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Benzyloxy-5-bromobenzaldehyde and ethyl 4-aminomethylbenzoate were heated together at 100° C. for 1 hour. The mixture was cooled, dissolved in ethanol (100 ml) and sodium borohydride (1.3 g) was added. The mixture was stirred for 18 hours at ambient temperature, acidified with acetic acid and water (200 ml) was added. The mixture was extracted with diethyl ether (4×100 ml), the extracts washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate which was purified by chromatography on silica gel eluting with CH2Cl2 then 5% ethyl acetate/CH2Cl2 (yield 11.4 g).

Workup

  1. temperatureThe mixture was cooled
  2. additionwas added
  3. extractionThe mixture was extracted with diethyl ether (4×100 ml)
  4. washthe extracts washed with saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ac2592b1d7e9403f99739f686d9d8a9c
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

Loading…