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Dimethylformamide → HCID 12899798, compound

HRID 2166757
Notes
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Reaction equation

HRID 2166757 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:25]1[CH2:26][CH2:27][N:22]([CH2:2][CH2:3][CH2:4][O:5][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:23][CH2:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 20229774HCID 20229774, compound

Product 1

HCID 12899798HCID 12899798, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.5 g of 1-(3-chloropropoxy)-1,4-diphenylbutane, 7 ml of morpholine, 1.5 g of potassium carbonate and 15 ml of dimethylformamide was heated at 100° C. for 1 hour. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on silica gel to give 1-(3-morpholinopropoxy)-1,4-diphenylbutane. M.P., 138°-139° C. (oxalate).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-650f6caad34b4f948057a9032a71c6d7
Source dataset
uspto-grants-1983_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04388469

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes