4-Nitrobenzyl bromide → HCID 19045475, compound

HRID 1781414Notes

Reaction equation

HRID 1781414 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C:10]1([CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH2:12][CH2:11]1)[NH:9][CH2:8][C:7]2=[O:32].[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)([O-:35])=[O:34]>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C:10]1([CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)[CH2:12][CH2:11]1)[N:9]([CH2:40][C:39]1[CH:42]=[CH:43][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=1)[CH2:8][C:7]2=[O:32]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 19045391HCID 19045391, compound

Product 1

HCID 19045475HCID 19045475, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6,7-dimethoxy-1'-[2-(4-nitrophenyl)ethyl]-spiro[1,2,3,4-tetrahydro-isoquinoline- 1,4'-piperidin]-4-one hydrochloride (0.33 g) sodium bicarbonate (0.1 g) and p-nitrobenzylbromide (0.25 g) in ethanol were refluxed for 18 hours. The reaction was concentrated and chromotographed on silica (methylene chloride/methanol, 90:10) to give 60 mg upon concentration and crystallization of the dihydrochloride salt from isopropanol. mp 174°-177° C.

Workup

  1. temperaturewere refluxed for 18 hours
  2. concentrationThe reaction was concentrated
  3. customto give 60 mg
  4. concentrationupon concentration and crystallization of the dihydrochloride salt from isopropanol

Sources & evidence

ORD record
ord-029cb54ee0db440182eaf2a51a27ca49
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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