4-Hydroxybenzaldehyde → HCID 12323413, compound

HRID 1655664Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11]1>>[OH:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[C:11]2/[C:10](=[O:15])[CH2:14][CH2:13][CH2:12]/2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 8452Cyclopentanone

Product 1

HCID 12323413HCID 12323413, compound

Procedure

The procedure was similar to that in Example 4 by reacting 4-hydroxybenzaldehyde with the morpholine enamine of cyclopentanone to give 2-(E)-[(4-hydroxy) benzylidene]cyclopentanone. The melting point of this intermediate compound was determined to be 188°-190° C. A subsequent Mannich reaction yielded the 2-Dimethylaminomethyl-5-(E)-[(4-hydroxy) benzylidene] cyclopentanone hydrochloride. The melting point of the product was determined to be 174°-175° C.

Sources & evidence

ORD record: ord-0d62442f9687412c88379840a40327e5
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250735

Reaction notes

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