Acetic Acid → HCID 10207981, compound

HRID 2221080Notes

Reaction equation

HRID 2221080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH:22]=O)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:24]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:30].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:34]2[CH2:33][CH2:32][CH:31]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C:25]3=[O:30])[CH2:36][CH2:35]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 21839852[1,4'-Bipiperidin]-2-one

Product 1

HCID 10207981HCID 10207981, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

(S)—N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (0.78 g) in methanol (3 mL) was added to a solution of [1,4′]bipiperidinyl-2-one (0.34 g) and acetic acid (0.15 mL) in methanol (8 mL). After 10 minutes, sodium cyanoborohydride (0.17 g) in methanol (4 mL) was added in a single portion. After being stirred overnight, the reaction mixture was diluted with saturated aqueous sodium bicarbonate, stirred for 30 minutes, and extracted with dichloromethane (4×50 mL). The organic extracts were dried, evaporated, and purified by chromatography, with dichloromethane:methanol (gradient 95:5, 90:10) as eluent to give the title compound (0.95 g). MS: m/z=516(M+). The product was dissolved in methanol (2 mL) and citric acid was added. The solution was concentrated and the residue was triturated with ether. The product was obtained as a white foam (1.2 g).

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane (4×50 mL)
  3. customThe organic extracts were dried
  4. customevaporated
  5. custompurified by chromatography, with dichloromethane

Sources & evidence

ORD record
ord-876dc7352ca84eb78283d770c4fc311d
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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