Iodine → 1-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide

HRID 2072471Notes

Reaction equation

HRID 2072471 reaction equation
[NH:1]([C:8]1([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].II>C1(C)C=CC=CC=1.C(Cl)Cl>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH2:28][C:19]=1[CH2:18][N:11]1[CH2:10][CH2:9][C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 964284-Anilinopiperidine-4-carboxamideHCID 127714333-(Chloromethyl)-1,2-dihydronaphthalene

Product 1

HCID 214082231-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-anilino isonipecotamide (5.5 g), 3,4-dihydro-2-chloromethylnaphthalene (4.0 g), and powdered sodium carbonate (3.5 g) in toluene (200 ml) containing several crystals of iodine is refluxed for 14 hours with vigorous stirring under nitrogen. The reaction mixture is then cooled, diluted with methylene chloride (100 ml), and filtered. The filtrate is concentrated and the crude product triturated with ethyl acetate (100 ml) to give the title compound.

Workup

  1. temperatureis refluxed for 14 hours
  2. temperatureThe reaction mixture is then cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe crude product triturated with ethyl acetate (100 ml)

Sources & evidence

ORD record
ord-489e56ecdefa4457972d39fdb2be6887
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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