2-(Dimethylamino)ethanol → HCID 21162745, compound

HRID 894195Notes

Reaction equation

HRID 894195 reaction equation
Cl[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][O:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[C:9](=[O:18])[C:8]=2[CH:19]=1)=[O:3].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24]>O1CCCC1>[O:18]=[C:9]1[C:8]2[CH:19]=[C:4]([C:2]([O:24][CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])=[O:3])[CH:5]=[CH:6][C:7]=2[CH2:13][O:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=2

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 21162714HCID 21162714, compound

Product 1

HCID 21162745HCID 21162745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1.0 gm of 9-chlorocarbonyl-6,11-dihydro-11-oxo-dibenz[b,e]oxepin as prepared in Example 10, Step A, in 10 cc of anhydrous tetrahydrofuran with stirring and add 2 ml of N,N-dimethylethanolamine. Stir at room temperature for 18 hours and strip the mixture to dryness. Partition the residue between ether and dilute hydrochloric acid and separate the aqueous layer. Basify the aqueous layer with aqueous ammonia and extract with ethyl acetate. Evaporate the organic phase and chromatograph the residue over silica-gel eluting with 90% chloroform in methanol to obtain the title product.

Workup

  1. stirringStir at room temperature for 18 hours
  2. customPartition the residue between ether and dilute hydrochloric acid
  3. customseparate the aqueous layer
  4. extractionBasify the aqueous layer with aqueous ammonia and extract with ethyl acetate
  5. customEvaporate the organic phase and chromatograph the residue over silica-gel
  6. washeluting with 90% chloroform in methanol

Sources & evidence

ORD record
ord-d19aea95bd2b4e32b218ee29788bb0e5
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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