Benzene, (3-bromopropoxy)- → HCID 67027739, compound

HRID 2192358Notes

Reaction equation

HRID 2192358 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@H:14]([O:20][C:21]([C:23]1([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:13]2>C(#N)C>[CH:21]([O-:22])=[O:20].[O:1]([CH2:8][CH2:9][CH2:10][N+:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@H:14]([O:20][C:21]([C:23]1([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 58348398HCID 58348398, compound

Product 1

HCID 67027739HCID 67027739, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-phenoxypropyl bromide (0.026 mL) was added to a solution of 1-phenyl -cycloheptanecarboxylic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 33a) (50 mg) in acetonitrile (1 mL). The reaction mixture was allowed to stir at room temperature for 72 hrs then heated to 50° C. for 3 days. The volatiles were evaporated and the residue purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give 57 mg of a hygroscopic foam. Further purification was achieved by reverse phase HPLC using a C18 column eluting with 5-95% MeCN/H2O containing 0.1% formic acid ° over 30 mins gave the title compound (43 mg) as an oil.

Workup

  1. temperaturethen heated to 50° C. for 3 days
  2. customThe volatiles were evaporated
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 0-10% MeOH/dichloromethane
  5. customto give 57 mg of a hygroscopic foam
  6. customFurther purification
  7. washeluting with 5-95% MeCN/H2O containing 0.1% formic acid ° over 30 mins

Sources & evidence

ORD record
ord-9105524989b14a479e53d57682213ed1
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

Loading…