4-Hydroxybenzamide → HCID 13320258, compound

HRID 1381231Notes

Reaction equation

HRID 1381231 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][CH:16]=1>C(OCC)(=O)C>[OH:13][C@@H:10]1[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][C@H:11]1[O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 650524-HydroxybenzamideHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320258HCID 13320258, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 28 g. of 1-benzyl-3,4-epoxypyrrolidine and 20.6 g. of 4-hydroxybenzamide was heated at 130° C. for 8 hrs. The cooled mixture was columned on silica gel using 5% methanol in ethyl acetate to elute the product, which was then crystallized from chloroform-benzene-methanol. The yield was 19% of product melting at 133.0°-6.0° C.

Workup

  1. additionA mixture of 28 g
  2. washto elute the product, which
  3. customwas then crystallized from chloroform-benzene-methanol

Sources & evidence

ORD record
ord-f4b31b39c579481088b02cc5a28f1d2e
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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