Phenylethanolamine → HCID 458553, compound

HRID 1004487Notes

Reaction equation

HRID 1004487 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:13].C(N(CC)CC)C>C(Cl)Cl>[OH:13][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 458553HCID 458553, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl chloride (16.9 ml, 0.146 moles) in 200 ml of methylene chloride was added under nitrogen dropwise over approximately 1 hour to a solution of 2-amino-1-phenylethanol (20.0 g, 0.146 moles) and triethylamine (20.0 ml, 0.146 moles) in 300 ml of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for 2 hours and then at room temperature for approximately 2 hours. The solid formed was collected by filtration and dried to give N-(2-hydroxy-2-phenyl-ethyl)-benzamide (20.33 g, 58%) as a white solid, mp 140-143° C.

Workup

  1. additionAfter the addition the reaction
  2. waitat room temperature for approximately 2 hours
  3. customThe solid formed
  4. filtrationwas collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-46eae542d5cf47dcb54b85165b204c09
Source dataset
uspto-grants-2000_04
Patent number
US06049006

Reaction notes

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