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

HRID 1730331
Notes
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Reaction equation

HRID 1730331 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-5adfb4ec915c40b7b64198cf0064d022
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03992389

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes