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

HRID 437219Notes

Reaction equation

HRID 437219 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(NC(C)C)(C)C.[I-].[Na+]>CN(C)C=O.O>[C:4]1([CH2:3][CH2:2][N:26]2[CH2:27][CH2:28][CH:23]([NH:22][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:24][CH2:25]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 118120N-4-PiperidylbenzamideHCID 1395411-(2-Bromoethyl)naphthalene

Product 1

HCID 214306091-[2-(1-Naphthyl)ethyl]-4-benzamidopiperidineYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1-(2-Bromoethyl)naphthalene (3.0 g.) was added to a solution of 4-benzamidopiperidine (3.0 g.), di-isopropylamine (4 ml.) and a trace of sodium iodide in dimethylformamide (10 ml.). The mixture was heated at 70° C. overnight, then poured into water and extracted with methylene chloride. The washed and dried extracts were evaporated and the residue was recrystallised from benzene to give the title compound (3.0 g.), m.p. 160°-162° C. (Found: C, 80.5; H, 7.4; N, 7.5 C24H26N2O requires C, 80.4; H, 7.3; N, 7.8%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe washed
  3. customdried extracts
  4. customwere evaporated
  5. customthe residue was recrystallised from benzene

Sources & evidence

ORD record
ord-b87f60e2c4174f2f9c871af09f7d99f4
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

Loading…