2-(Dimethylamino)ethanol → HCID 21419736, compound

HRID 441676Notes

Reaction equation

HRID 441676 reaction equation
Cl[C:2]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=1)=[O:3].CN(C)CC[OH:25]>O1CCCC1>[C:2]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=1)([OH:25])=[O:3]

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 21419719HCID 21419719, compound

Product 1

HCID 21419736HCID 21419736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 G. of 2-chlorocarbonyl-9-chloro-5-oxo-5H-dibenzo[a,d]cycloheptene, as prepared in Example VIII, is dissolved in 10 ml. of anhydrous tetrahydrofuran with stirring, and treated with 2 ml. of dimethylethanolamine. After the solution is stirred for 16 hours, it is evaporated. The residue is partitioned between ether and dilute hydrochloric acid. The aqueous layer is basified with aqueous ammonia and extracted with ethyl acetate. This solution is evaporated and the residue chromatographed on silica gel, eluting with 10:90:1 methanol:chloroform:triethylamine, to afford the β-N,N-dimethylaminoethyl ester of 2-carboxy-9-chloro-5-oxo-5H-dibenzo[a,d]cycloheptene as an oil.

Workup

  1. dissolutionis dissolved in 10 ml
  2. additiontreated with 2 ml
  3. customit is evaporated
  4. customThe residue is partitioned between ether and dilute hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. customThis solution is evaporated
  7. customthe residue chromatographed on silica gel
  8. washeluting with 10:90:1 methanol

Sources & evidence

ORD record
ord-b9f61466a3d24032bef45c2927aa5b81
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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