Dimethylformamide → HCID 20567167, compound

HRID 847747Notes

Reaction equation

HRID 847747 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].C[N:33](C)C=O>>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:31])[C:23]2[C:24](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([NH2:33])=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 20567167HCID 20567167, compound

Procedure

15 g of 3-(1-piperidinylmethyl)phenol was dissolved in 80 ml of dry dimethylformamide. The solution was gradually added dropwise to a suspension of 3.14 g of 60% sodium hydride in 30 ml of dry dimethylformamide with stirring under ice cooling. After the addition, the mixture was stirred at room temperature for 20 minutes, and 21 g of N-bromopropylphthalimide was added. The mixture was reacted at room temperature for 1 hour, and ice water was added. The mixture was extracted with chloroform, washed with water and dried over anhydrous magnesium sulfate. Distilling off the solvent afforded 28.5 g of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]phthalamide as an oil.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. customThe mixture was reacted at room temperature for 1 hour
  4. extractionThe mixture was extracted with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationDistilling off the solvent

Sources & evidence

ORD record
ord-9ef6fac505944d61b26ea0caf52831b4
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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