Diisopropylamine → 1-[2-(Cyclohexyl)ethyl]-4-benzamidopiperidine

HRID 1730324Notes

Reaction equation

HRID 1730324 reaction equation
[CH:1]1([CH2:7][CH2:8]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]([NH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(NC(C)C)(C)C.[I-]>CN(C)C=O.O>[CH:1]1([CH2:7][CH2:8][N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:20][CH2:21]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 15440(2-Bromoethyl)cyclohexaneHCID 30165Iodide IonHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 214132691-[2-(Cyclohexyl)ethyl]-4-benzamidopiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Cyclohexylethyl bromide (1.9 g.) in dimethylformamide (10 ml.) was added to 4-benzamidopiperidine (2.2 g.), diisopropylamine (4 ml.) and a trace ofsodium iodide in dimethylformamide (10 ml.). The mixture was heated at 70° C for 16 hours, cooled, poured into water, and extracted with methylene chloride. The washed and dried extracts were evaporated and the solid residue was recrystallised from ethanol to give the product (1.25 g.), m.p. 174°-5° C. (Found: C, 76.4; H, 9.5; N, 8.9. C20H30H2O requires C, 76.4; H, 9.6; N, 8.9%).

Workup

  1. temperaturecooled
  2. extractionextracted with methylene chloride
  3. washThe washed
  4. customdried extracts
  5. customwere evaporated
  6. customthe solid residue was recrystallised from ethanol
  7. customto give the product (1.25 g.), m.p. 174°-5° C. (Found: C, 76.4; H, 9.5; N, 8.9. C20H30H2O requires C, 76.4; H, 9.6; N, 8.9%)

Sources & evidence

ORD record
ord-b3ba807153204e05900ae303a2c83fb5
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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