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

HRID 2071271Notes

Reaction equation

HRID 2071271 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-].[Na+]>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 5238Sodium IodideHCID 7912DiisopropylamineHCID 15440(2-Bromoethyl)cyclohexaneHCID 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 of sodium 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 produce (1.25 g.), m.p. 174°-5° C. (Found: C, 76.4; H, 9.5; N, 8.9. C20H30N2O 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
  8. customproduce (1.25 g.), m.p. 174°-5° C. (Found: C, 76.4; H, 9.5; N, 8.9. C20H30N2O requires C, 76.4; H, 9.6; N, 8.9%)

Sources & evidence

ORD record
ord-8eb2a136dec44079b3fbc05620ab5696
Source dataset
uspto-grants-1977_09
Patent number
US04046767

Reaction notes

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