3-(3-Bromopropyl)benzamide → N-[3-(3-carbamoylphenyl)propyl]phthalimide

HRID 1608727Notes

Reaction equation

HRID 1608727 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH2:10])=[O:9].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[C:8]([C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][N:18]2[C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:24])[CH:13]=[CH:12][CH:11]=1)(=[O:9])[NH2:10]

Participants

4

Reactant 2

HCID 193772323-(3-Bromopropyl)benzamide2×HCID 24194345Phthalimide potassium salt

Product 1

HCID 19377229N-[3-(3-carbamoylphenyl)propyl]phthalimideYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.0 g (0.057 mole) 3-(3-bromopropyl)benzamide (the product of step (d)), 11.5 g potassium phthalimide and 26.3 ml dimethylformamide was heated to reflux under argon gas for four hours. The heat source was removed and the mixture was stirred to cool to room temperature. Water (about 85 ml) was added. The resulting slurry was stirred for 20 minutes, then filtered and washed three times with about 50 ml cold water (each wash made a slurry solution in the funnel). The solids were then washed with about 20 ml cold 1:1 isopropyl alcohol: water and dried under vacuum overnight to give 17.04 g of the above-identified product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon gas for four hours
  3. customThe heat source was removed
  4. additionWater (about 85 ml) was added
  5. stirringThe resulting slurry was stirred for 20 minutes
  6. filtrationfiltered
  7. washwashed three times with about 50 ml cold water (each wash
  8. washThe solids were then washed with about 20 ml cold 1:1 isopropyl alcohol
  9. dry with materialwater and dried under vacuum overnight

Sources & evidence

ORD record
ord-42c932a66c4b4006b116d1ae570da55f
Source dataset
uspto-grants-1995_03
Patent number
US05395970

Reaction notes

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