4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 71487937, compound

HRID 1518947Notes

Reaction equation

HRID 1518947 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]Cl)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([OH:37])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1>CN(C=O)C>[C:18]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:34]3[CH2:33][CH2:32][C:31]([C:28]4[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=4)([OH:37])[CH2:36][CH2:35]3)[CH2:10][CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 10936372Piperazine, 1-(3-chloropropyl)-4-(diphenylmethyl)-

Product 1

HCID 71487937HCID 71487937, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In DMF, 9.0 g of 1-[4-(diphenylmethyl)piperazinyl]-3-chloropropane (2.0 eq) and 4-(4-chlorophenyl)-4-hydroxypiperidine (2.0 eq.) were dissolved (20 v/w), and the obtained solution was heated to reflux at 80° C. for 6 hours. The solution was allowed to cool and then concentrated, and purified by silica gel column chromatography (Wakogel C-200, 100 g) to obtain 8.3 g of 1-[4-(diphenylmethyl)piperazinyl]-3-[4-(4-chlorophenyl)-4-hydroxy-piperidinyl]propane (yield 60.1%), which is a target compound, as a white solid in an amorphous state.

Workup

  1. temperaturethe obtained solution was heated
  2. temperatureto cool
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (Wakogel C-200, 100 g)

Sources & evidence

ORD record
ord-78617c040a7f4be98d9d46605d40ab6b
Source dataset
uspto-grants-2015_07
Patent number
US09073861B2

Reaction notes

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