Morpholine → HCID 19004446, compound

HRID 2225805Notes

Reaction equation

HRID 2225805 reaction equation
C[O:2][C:3](=[O:35])[C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12]/[CH:13]=[CH:14]/[C:15]2[N:16]([CH:31]([CH3:33])[CH3:32])[C:17]3[C:22]([C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:7][CH:6]=1.[OH-].[Na+].N1CCOCC1>CO.C(OCC)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH:31]([CH3:33])[CH3:32])[C:15]=2/[CH:14]=[CH:13]/[CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:34])[C:3]([OH:35])=[O:2])=[CH:10][CH:9]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 67757908HCID 67757908, compound

Product 1

HCID 19004446HCID 19004446, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

As in Example 19, (E)-4-[3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-propenyloxy]-alpha-oxobenzeneacetic acid methyl ester (0.354 g) in methanol (5 mL) was treated with 1N sodium hydroxide (0.9 mL). The usual work up gave 0.4 g of a oil, which was dissolved in diethyl ether and morpholine (0.07 g) was added. Crystallization was induced and the recovered solid was recrystallized from dichloromethane-ethyl acetate to provide 0.26 g of (E)-4-[3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indole-2-yl]-2-propenyloxy]-alpha-oxobenzeneacetic acid (1:1) morpholine salt as a colorless solid, mp 151°-152° C.

Workup

  1. customCrystallization
  2. customthe recovered solid was recrystallized from dichloromethane-ethyl acetate

Sources & evidence

ORD record
ord-101136dfa2bf4af09af1f5af9d495840
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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