Styrene Oxide → HCID 10409887, compound

HRID 1462363Notes

Reaction equation

HRID 1462363 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1[OH:22])(=[O:3])[NH2:2].[C:23]1([CH:29]2[O:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:30][CH:29]([OH:31])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][C:5]=1[OH:22])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 20452666HCID 20452666, compound

Product 1

HCID 10409887HCID 10409887, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 12.7 g of N-[3-(4-carbamoyl-3-hydroxy-phenoxy)propyl]-benzylamine and 7.6 g of phenylethylene oxide in 80 ml of isopropanol is refluxed for 16 hours. The reaction mixture is evaporated, the residue is partitioned between 100 ml of 6N hydrochloric acid and 100 ml of ether and the aqueous phase is separated off and rendered alkaline with 2N ammonia solution. The N-[3-(4-carbamoyl-3-hydroxy-phenoxy)-propyl]-N-(2-hydroxy-2-phenyl-ethyl]-benzylamine thus obtained is isolated by extraction with ethyl acetate an debenzylated in the form of the crude product.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is partitioned between 100 ml of 6N hydrochloric acid and 100 ml of ether
  3. customthe aqueous phase is separated off

Sources & evidence

ORD record
ord-2b85d50f46e3481ca4e264887231d390
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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