Benzoyl chloride → HCID 178513415, compound

HRID 858171Notes

Reaction equation

HRID 858171 reaction equation
[OH:1][CH:2]([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[NH:7].[OH-].[Na+].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42]>C1C=CC=CC=1>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42].[C:23]([O:1][CH:2]([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[NH:7])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 7412Benzoyl chloride2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 178513416HCID 178513416, compound

Product 1

HCID 178513415HCID 178513415, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.9 g (75.0 mmol) of N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridine-carboximidamide [Hung. Pat. 177.578 (1976)] was dissolved in 300 ml of benzene. To this solution 150 ml of 1 N sodium hydroxide solution was added, followed by dropwise addition of 19.5 ml (168 mmol) of benzoyl chloride. After stirring the mixture intensively for 2 hours, 7.1 g (67 mmol) of sodium carbonate and a further portion of benzoyl chloride (9.75 ml; 84 mmol) was added, and the stirring was continued overnight. The phases were then separated, the organic layer was extracted with 1 N sodium hydroxide solution and water, dried and evaporated to dryness. The residue (41 g oil) was dissolved in 150 ml of acetone, and 8.7 g (75 mmol) maleic acid was added. The obtained precipitate was filtered off, washed with acetone, and dried.

Workup

  1. waitthe stirring was continued overnight
  2. customThe phases were then separated
  3. extractionthe organic layer was extracted with 1 N sodium hydroxide solution and water
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue (41 g oil) was dissolved in 150 ml of acetone
  7. filtrationThe obtained precipitate was filtered off
  8. washwashed with acetone
  9. customdried

Sources & evidence

ORD record
ord-929e8946a230497e819bd32e634d8a0b
Source dataset
uspto-grants-2006_12
Patent number
US07148239B2

Reaction notes

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