Water → HCID 21393741, compound

HRID 461448Notes

Reaction equation

HRID 461448 reaction equation
[N:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[Cl:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>CCOCC>[ClH:23].[ClH:23].[N:1]1([CH2:7][C:8]2[C:17]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 204543Piperidine, 1-(2-naphthalenylmethyl)- (9CI)HCID 11974404N-chloromethylpiperidineHCID 178418339Butyllithium

Product 1

HCID 21393741HCID 21393741, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-piperidinomethylnaphthalene (5.6 g) in dry ether (200 ml) was added, under nitrogen, a 1.5M ethereal solution of butyl lithium (18.3 ml) and the mixture was kept at room temperature for 24 hours. N-(Chloromethyl)piperidine (7.34 g) was added, the mixture was heated under reflux for 1 hour, and poured into water (1 l). The precipitated material was extracted into ether, the extract was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was purified by chromatography on silica and an ethereal solution of the product was treated with ethereal hydrogen chloride. 1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionThe precipitated material was extracted into ether
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on silica
  8. additionan ethereal solution of the product was treated with ethereal hydrogen chloride
  9. custom1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°

Sources & evidence

ORD record
ord-4150f064f5894e67a7a8a6d4a73e9703
Source dataset
uspto-grants-1977_12
Patent number
US04062955

Reaction notes

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