Ethanolamine → N-(2-Hydroxyethyl)-4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzamide

HRID 2395071Notes

Reaction equation

HRID 2395071 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:28]([CH2:30][NH2:31])[OH:29]>>[OH:29][CH2:28][CH2:30][NH:31][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:10]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 18973721Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate

Product 1

HCID 18974052N-(2-Hydroxyethyl)-4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzamideYield 29%

Conditions

Temperature
160 °C

Procedure

Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.20 g, 0.576 mmol) was dissolved in ethanolamine (3 ml) and heated to 160° C. under argon for 2 hours. Water was added (3 ml) and the aqueous layers were extracted with ethyl acetate and the organic phase was dried (MgSO4) and evaporated. The residue was recrystallised from EtOAc/hexane and washed with ether to give the title product (0.064 g, 29%).

Workup

  1. extractionthe aqueous layers were extracted with ethyl acetate
  2. dry with materialthe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe residue was recrystallised from EtOAc/hexane
  5. washwashed with ether

Sources & evidence

ORD record
ord-11a32ba38e184353845bf981589864a9
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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