Acetic Acid → HCID 20145287, compound

HRID 648639Notes

Reaction equation

HRID 648639 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[C:5](O)(=O)C.N[C:10]1[CH:11]=[CH:12][C:13]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:14]([CH:16]([CH:18]([C:28]([NH2:30])=[O:29])[C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH3:17])[CH:15]=1.C=O>C(#N)C.CN(C)C=O>[CH3:5][N:2]([CH3:1])[C:10]1[CH:11]=[CH:12][C:13]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:14]([CH:16]([CH:18]([C:28]([NH2:30])=[O:29])[C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH3:17])[CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20145241HCID 20145241, compound

Product 1

HCID 20145287HCID 20145287, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A tenth of a gram (1.589 m mol) of sodium cyanoborohydride and, after two minutes, 0.056 ml of glacial acetic acid were added at 20° C. to a stirred solution of 0.20 gm (0.5242 m mol) of 4-[(1-(5-amino-2-piperidino-phenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid and 0.45 ml of 40% formalin in 2 ml of acetonitrile and 1 ml of absolute dimethyl formamide. After 1.5 hours the reaction mixture was evaporated in vacuo. The evaporation residue was dissolved in water by addition of hydrochloric acid at a pH of 2 to 3. After extraction with chloroform several times the aqueous phase was adjusted to a pH of 6 to 7 by means of saturated sodium bicarbonate solution and extracted several times with chloroform. This organic extract was dried and filtered. After evaporation in vacuo the evaporation residue was recrystallized from isopropanol. The colorless crystals were washed with absolute ether.

Workup

  1. customAfter 1.5 hours the reaction mixture was evaporated in vacuo
  2. dissolutionThe evaporation residue was dissolved in water by addition of hydrochloric acid at a pH of 2 to 3
  3. extractionAfter extraction with chloroform several times the aqueous phase
  4. extractionextracted several times with chloroform
  5. extractionThis organic extract
  6. customwas dried
  7. filtrationfiltered
  8. customAfter evaporation in vacuo the evaporation residue
  9. customwas recrystallized from isopropanol
  10. washThe colorless crystals were washed with absolute ether

Sources & evidence

ORD record
ord-a68044cfcaed4a71b252f541f8e45ada
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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