Acetic Anhydride → 3-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

HRID 986698Notes

Reaction equation

HRID 986698 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18])=[CH:15][C:14]=2[Br:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[O:18])=[CH:15][C:14]=2[Br:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[O:34][C:35](=[O:37])[CH3:36])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 137681403-(N,N-dimethylamino)propyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate

Product 1

HCID 137456293-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a mixture of pyridine (5 ml) and acetic anhydride (5 ml) was dissolved 3-(N,N-dimethylamino)propyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate (1 g). The solution was stirred at 110° to 120° C. for about 18 hours, followed by concentration. The residue was chromatographed on a column of silica gel. The elution was conducted with ethyl acetate, and the eluate was evaporated. The resulting oily substance was dissolved in ether, to which was added an ether solution of anhydrous oxalic acid. The resultant crystals were collected by filtration, which were washed with ethanol and then with isopropyl ether, followed by drying to give 866 mg of 3-(N,N-dimethyl-amino)propyl 4-[3-(4-acetyl-3-acetoxy-2-propylphenoxy)propoxy]-3-bromobenzoate.mono-oxalate, m.p. 141°-142° C.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue was chromatographed on a column of silica gel
  3. washThe elution
  4. customthe eluate was evaporated
  5. dissolutionThe resulting oily substance was dissolved in ether, to which
  6. additionwas added an ether solution of anhydrous oxalic acid
  7. filtrationThe resultant crystals were collected by filtration, which
  8. washwere washed with ethanol
  9. customby drying

Sources & evidence

ORD record
ord-0326efcbcf7d4fffb6e9e75556b33592
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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