Triethylamine → HCID 58258314, compound

HRID 514590Notes

Reaction equation

HRID 514590 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[Cl:10].[CH3:11][CH2:12][N:13](CC)[CH2:14][CH3:15].N1CCCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:13]2[CH2:14][CH2:15][CH2:11][CH2:12]2)=[CH:4][C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 233343071-Bromo-2-chloro-4-(chloromethyl)benzene

Product 1

HCID 58258314HCID 58258314, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-2-chloro-4-(chloromethyl)-benzene (25.2 g, 105.03 mmol) and Et3N (16.1 ml, 115.53 mmol) in THF (150 ml) was stirred at r.t. Pyrrolidine (8.2 g, 115.53 mmol) was added dropwise. The r.m. was stirred overnight at r.t. and was then concentrated in vacuo. The residue was taken up into water and extracted with CH2Cl2 (3×100 ml). The combined organic layer was washed with saturated NaHCO3 and brine, and was then dried (MgSO4), filtered and the solvent was evaporated in vacuo. Yield: 25.8 g of 1-[(4-bromo-3-chlorophenyl)methyl]-pyrrolidine (90% yield, crude product; used in next reaction step, without further purification).

Workup

  1. concentrationwas then concentrated in vacuo
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. washThe combined organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialwas then dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6a8605a3396c4b34970f6139581df791
Source dataset
uspto-grants-2015_08
Patent number
US09107946B2

Reaction notes

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