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

HRID 437212Notes

Reaction equation

HRID 437212 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 (2.2g.), 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 product (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 product (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-d41b5da9e0554207a405cb8fb59311e2
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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