Ammonia → Roxatidine

HRID 847738Notes

Reaction equation

HRID 847738 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:19][CH2:20][C:21](O)=[O:22].N>O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20](=[O:19])[CH2:21][OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 757Glycolic AcidHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 91276RoxatidineYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.59 g of 3-[3-(1-piperidinylmethyl)phenoxy]propylamine and 536 mg of hydroxyacetic acid were heated at 200° C. for 2 hours. The reaction mixture was cooled, and water was added. The mixture was alkalized with aqueous ammonia, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to afford 1.86 g of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydroxyacetamide.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-aefa9d752e97463fb78632850c5f4ee1
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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