4-Chloro-4'-hydroxybutyrophenone → HCID 21430600, compound

HRID 1730358Notes

Reaction equation

HRID 1730358 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:6].[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[ClH:1].[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[O:6])[CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 815784-Chloro-4'-hydroxybutyrophenoneHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 21430600HCID 21430600, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-(4-Chlorobutyryl)phenol (130 g 4-benzamidopiperidine (134 g) triethylamine (70 g.) and dimethylformamide were stirred at 60° C for 2 days allowed to stand overnight then filtered. The filtrate was diluted with a large volume of diethyl ether whereupon an oil precipitatedwhich crystallised after being allowed to stand. This precipitate was filtered off, washed with diethyl ether then water, dried and converted tothe hydrochloride using hydrogen chloride gas dissolved in a mixture of isopropyl alcohol and ethanol to afford 4-benzamido-1-[4-(4-hydroxyphenyl)-4-oxobutyl]piperidine hydrochloride (43.5 g. 16%) m.p. 276° C. Analysis: Found: C, 65.60; H, 6.73; N, 6.75% C22H26N2O3HCl requires C, 65.80; H, 6.78; N,6.97%.

Workup

  1. filtrationthen filtered
  2. additionThe filtrate was diluted with a large volume of diethyl ether whereupon an oil precipitatedwhich
  3. customcrystallised
  4. filtrationThis precipitate was filtered off
  5. washwashed with diethyl ether
  6. dry with materialwater, dried
  7. dissolutiondissolved in a mixture of isopropyl alcohol and ethanol

Sources & evidence

ORD record
ord-33c5d9ed70034ce1ba2317b90895fca9
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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