Benzyl Chloride → HCID 11220894, compound

HRID 2298437Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])[CH2:17][CH2:16]1>C(O)(=O)C>[CH2:7]([N:15]1[CH2:16][CH2:17][CH:18]([CH2:21][CH:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:20]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 62.5 °C

Procedure

Sodium carbonate (1,550 g) and benzyl chloride (582.3 g) were added to the solution of the acetic acid salt of dimethyl (4-piperidylmethyl)malonate [XXIXa] from the previous step. The obtained slurry was stirred for 12 hours at 60-65° C. and evaporated under reduced pressure. Water was added to the residue and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, passed through short silica gel column and evaporated under reduced pressure. The residue was washed with hexane and dried under reduced pressure to give dimethyl (N-benzyl-4-piperidylmethyl)malonate [XXIIa]. 1H NMR (CDCl3) δ1.10-1.37 (m, 3H), 1.50-1.75 (m, 2H), 1.75-2.00 (m, 4H), 2.83 (br. d, 2H, J=12 Hz), 3.44 (s, 2H), 3.70 (s, 6H), 7.26 (m, 5H).

Workup

customevaporated under reduced pressure
additionWater was added to the residue
extractionthe mixture was extracted with dichloromethane
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
washThe residue was washed with hexane
customdried under reduced pressure

Sources & evidence

ORD record: ord-22b38f63754a43a88c68701a89ad13cf
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492522B1

Reaction notes

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