Triethylamine → alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 54686Notes

Reaction equation

HRID 54686 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH:25]=O)[N:24]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.[BH4-].[Na+]>CO>[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH:2][CH2:3][CH:4]([OH:15])[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)[N:24]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamide

Product 1

HCID 14719582alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcoholYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-(Aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride (2.88 g) and 2-acetamido-4-formyl-thiazole (2.1 g) were suspended in 14 ml methanol, and 1.8 ml triethylamine was added dropwise to this suspension with stirring. The resulting solution was heated under reflux for 30 minutes, and 0.70 g sodium borohydride was added in small portions with stirring under ice cooling. The crystals which separated out were collected by filtration, washed with water and methanol in that order and vacuum-dried, giving 3.55 g of α-[[[(2-acetamido-4-thiazolyl)methyl]amino]methyl]-3,4dimethoxybenzyl alcohol, m.p. 204°-206° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 30 minutes
  3. stirringwith stirring under ice cooling
  4. customThe crystals which separated out
  5. filtrationwere collected by filtration
  6. washwashed with water and methanol in that order
  7. customvacuum-dried

Sources & evidence

ORD record
ord-b0d43046e79b46afa0790950d51ba04d
Source dataset
uspto-grants-1997_04
Patent number
US05623074

Reaction notes

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