Benzyl Bromide → HCID 16041936, compound

HRID 499684Notes

Reaction equation

HRID 499684 reaction equation
[N:1]12[CH2:7][C:4]([C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9]#[N:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[Br-:23].[C:9]([C:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]12[CH2:7][N+:1]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:6][CH2:5]1)[CH2:2][CH2:3]2)#[N:10]

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 42625857HCID 42625857, compound

Product 1

HCID 16041936HCID 16041936, compoundYield 59.7%

Conditions

Temperature
60 °C

Procedure

To a solution of 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)acetonitrile (0.044 g, 0.152 mmol) in 2CH3CN/3CHCl3 (3.5 mL) was added (bromomethyl)benzene (0.030 mL, 0.252 mmol). The solution was heated to 60° C. for 16 h. The reaction was cooled to room temperature and concentrated under vacuum. The residue was taken up in DMSO and purified by Gilson preparatory HPLC (without TFA) to give the title compound (0.0417 g, 59.6%). EI-MS m/z 451 (M+) Rt (1.20 min).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. custompurified by Gilson preparatory HPLC (without TFA)

Sources & evidence

ORD record
ord-09858e7b21a7451886bac77864b2b93a
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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