Benzyl Bromide → HCID 19045781, compound

HRID 1781509Notes

Reaction equation

HRID 1781509 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][C:9]1([CH2:14][CH2:13][CH2:12][CH2:11][NH:10]1)[CH2:8][CH2:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][C:9]1([CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19028964HCID 19028964, compound

Product 1

HCID 19045781HCID 19045781, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dihydro-6,7-dimethoxyspiro[naphthalene-2(1H),2'-piperidine] hydrochloride (10 mg) was treated with potassium carbonate (10 g) and benzyl bromide (4 ml) in DMF (300 ml) at 60° C. for 2 hours. The reaction product was extracted with ethyl acetate-water, washed with water, dried, and concentrated. Purification with silica gel column chromatography (eluent; ethyl acetate) gave 3,4-dihydro-6,7-dimethoxy-1'-benzylspiro[naphthalene-2(1H),2'-piperidine] (10.8 g) which was dissolved in hydrobromic acid (33 ml) at 60° C. After being refluxed for 1.5 hr, the reaction mixture was poured into water and neutralized with sodium bicarbonate followed by extraction with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was crystallized from hexane to give 3,4-dihydro-6,7-hydroxy-1'-benzylspiro[naphthalene-2(1H),2'-piperidine] (5.92 g).

Workup

  1. extractionThe reaction product was extracted with ethyl acetate-water
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customPurification with silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-92aedeabdb674b35aa10924e69d9fbbd
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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