4-Phenylpiperidin-4-ol → HCID 18964186, compound

HRID 2256026Notes

Reaction equation

HRID 2256026 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:22]([CH2:34][CH:35]=O)[CH2:23][N:24]([CH3:33])[C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:18]=[CH:19][C:20]=1[Cl:21].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:22]([CH2:34][CH2:35][N:5]2[CH2:6][CH2:7][C:2]([OH:1])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:3][CH2:4]2)[CH2:23][N:24]([CH3:33])[C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

7

Reactant 4

HCID 963874-Phenylpiperidin-4-olHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22137499N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Product 1

HCID 18964186HCID 18964186, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A solution of 4-hydroxy-4-phenyl-piperidine (1.99 g) in methanol (20 mL) was cooled to 0° C. and the pH was adjusted to 8 by adding acetic acid. To this solution was added N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (3.57 g) in methanol (20 mL), and the resulting reaction mixture was treated with sodium cyanoborohydride (0.765 g). Upon warming to the room temperature, the reaction mixture was stirred for 16 hours and treated with saturated sodium bicarbonate solution. The solution was extracted with dichloromethane, dried (anhydrous sodium sulfate) and evaporated. The resulting material was purified by chromatography, with dichloromethane:methanol (90:10) as the eluent, to give the piperidine (2.42 g); NMR (CDCl3): 1.5-2.5 (m, 10), 2.68 (broad, 4), 3.47 (s, 3), 3.5-3.57 (m, 1), 6.8-7.5 (m, 13); MS: m/z=511(M+1). This material was used in the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. extractionThe solution was extracted with dichloromethane
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated
  5. customThe resulting material was purified by chromatography, with dichloromethane:methanol (90:10) as the eluent

Sources & evidence

ORD record
ord-36ecf898827b420ea909d70eec679f5c
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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