1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 67027752, compound

HRID 2192368Notes

Reaction equation

HRID 2192368 reaction equation
[Br:1][CH2:2][CH2:3][O:4][CH2:5][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]([CH2:5][O: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 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67027645HCID 67027645, compound

Product 1

HCID 67027752HCID 67027752, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-bromo-ethoxymethyl)-benzonitrile (41 mg, 0.17 mmol) and 1-phenyl -cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (51 mg) in MeCN (1 mL) was stirred at room temperature for 16 h then heated to 80° C. under nitrogen overnight. The resulting solid was filtered off, washed with ether and dried under vacuum to give the title compound (70 mg) as a white solid.

Workup

  1. temperaturethen heated to 80° C. under nitrogen overnight
  2. filtrationThe resulting solid was filtered off
  3. washwashed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c331d1be3ca94054ac7b6935a247cc49
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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