Morpholine → HCID 53850075, compound

HRID 1729213Notes

Reaction equation

HRID 1729213 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([C:7](=[O:17])[C:8]2[CH:13]=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH:4]([C:18]([OH:20])=O)[CH2:3]1.C(N(CC)CC)C.ClC(OCC)=O.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[OH:1][CH:2]1[CH2:6][N:5]([C:7](=[O:17])[C:8]2[CH:13]=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH:4]([C:18]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:20])[CH2:3]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16771157HCID 16771157, compound

Product 1

HCID 53850075HCID 53850075, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.5 g (0.016 mol) of 4-hydroxy-1-(3,4-methylenedioxybenzoyl)pyrrolidine-2-carboxylic acid obtained in Example 6 are suspended in 110 ml of acetonitrile at 0° C. 1.1 equivalents of triethylamine are added and the reaction mixture is stirred for 30 minutes, then 1.1 equivalents of ethyl chloroformate are added while maintaining the temperature between 0° and 5° C. After stirring for 30 minutes, 1.1 equivalents of morpholine are added to the filtrate. One equivalent is stirred at room temperature for 2 hours. The precipitate is separated, the filtrate is evaporated under vacuum. The residue is recrystallized.

Workup

  1. temperaturewhile maintaining the temperature between 0° and 5° C
  2. stirringAfter stirring for 30 minutes
  3. stirringOne equivalent is stirred at room temperature for 2 hours
  4. customThe precipitate is separated
  5. customthe filtrate is evaporated under vacuum
  6. customThe residue is recrystallized

Sources & evidence

ORD record
ord-3c775398d0174535afb35618ce7a3abb
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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