Benzylamine → Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate

HRID 1582393Notes

Reaction equation

HRID 1582393 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](Br)[CH2:7][CH2:8][CH:9](Br)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:5].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1C=CC=CC=1>[CH3:1][CH2:2][O:3][C:4]([CH:6]1[N:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 241588Diethyl 2,5-dibromohexanedioate

Product 1

HCID 286120Diethyl 1-benzylpyrrolidine-2,5-dicarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of Diethyl meso-2,5-dibromoadipate (50 g, 139 mmol) in benzene (150 mL) was heated to reflux. Then heating was discontinued and benzylamine (50 mL) was added under stirring in 1 h. At the end of the addition, the mixture was refluxed for 20 h. After cooling down, the hydrobromide salt was filtered off and washed with benzene, and the benzene solution was evaporated. The residue was distilled under reduced pressure (180-190° C./0.3 mmHg) to give a product (39.9 g, 94%) as a yellow oil.

Workup

  1. temperatureThen heating
  2. additionAt the end of the addition
  3. temperaturethe mixture was refluxed for 20 h
  4. temperatureAfter cooling down
  5. filtrationthe hydrobromide salt was filtered off
  6. washwashed with benzene
  7. customthe benzene solution was evaporated
  8. distillationThe residue was distilled under reduced pressure (180-190° C./0.3 mmHg)

Sources & evidence

ORD record
ord-071c39e2bc004e888faa39e8e14472f4
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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