Triethylamine → HCID 58266622, compound

HRID 1505932Notes

Reaction equation

HRID 1505932 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:17]12[CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][NH:18]2>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:18]2[CH2:19][CH:20]3[CH2:23][CH:17]2[CH2:22][CH2:21]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 789632-Azabicyclo[2.2.1]heptane

Product 1

HCID 58266622HCID 58266622, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-bromobenzyl bromide (66 mg, 0.26 mmol), triethylamine (0.22 mL, 1.56 mmol) and 2-azabicyclo[2.2.1]heptane (71 mg, 0.52 mmol) in THF (10 mL) was heated under reflux for 5 h. The reaction mixture was cooled to ambient temperature, the solid removed by filtration and the filtrate concentrated under reduced pressure to afford the title compound (70 mg, quantitative yield) that was used in the next step without further purification. LCMS (Method B): RT=2.04 min, M+H+=266/268.

Workup

  1. temperatureunder reflux for 5 h
  2. customthe solid removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-348beab4909940ae8b539fa8b84ac1f8
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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