HCID 10879224, compound → HCID 53311259, compound

HRID 2192366Notes

Reaction equation

HRID 2192366 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([O:22][C:23]([C:25]1([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:15]2>CC#N>[Br-:1].[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH2:3][CH2:2][N+:14]23[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]2)[C@@H:16]([O:22][C:23]([C:25]2([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])[CH2:15]3)=[CH:7][CH:8]=1)#[N:11]

Participants

4

Reactant 2

HCID 10879224HCID 10879224, compoundHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 53311259HCID 53311259, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-bromo-propoxy)-benzonitrile (41 mg) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (52 mg) in MeCN (1 mL) was stirred at room temperature for 16 h then heated to 80° C. under nitrogen for a further 16 h. The volatiles were evaporated and the residue was triturated with ether to give an off-white solid that was triturated with EtOAc and dried under vacuum to give the title compound (61 mg) as a white solid.

Workup

  1. temperaturethen heated to 80° C. under nitrogen for a further 16 h
  2. customThe volatiles were evaporated
  3. customthe residue was triturated with ether
  4. customto give an off-white solid
  5. customthat was triturated with EtOAc
  6. customdried under vacuum

Sources & evidence

ORD record
ord-39b9c123d78548b099db57cc90d991cb
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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