Potassium Carbonate → 1-(4-(Diphenylmethyl)piperazinyl)pentane-3-ol

HRID 2297527Notes

Reaction equation

[C:1]1([CH:7]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH3:25])[CH2:18][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Diphenylmethylpiperazine (2.20 g) was dissolved in dimethylformamide (25 ml), and then 1-chloro-3-pentanol (1.78 g) and potassium carbonate (722 mg) were added thereto, followed by stirring the mixture at 80° C. for 15 hours. After evaporation of dimethylformamide, water was added to the residue and the resultant was extracted 3 times with ethyl acetate. Organic layers were combined and washed with brine. The resultant was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain 1.79 g of amorphous 1-(4-(diphenylmethyl)piperazinyl)pentane-3-ol. Yield: 61%.

Workup

customAfter evaporation of dimethylformamide, water
additionwas added to the residue
extractionthe resultant was extracted 3 times with ethyl acetate
washwashed with brine
dry with materialThe resultant was dried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-cf5e1207608e4825930853d12d59ea2b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492364B1

Reaction notes

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