Dimethylformamide → HCID 10506075, compound

HRID 2107654Notes

Reaction equation

HRID 2107654 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:4][C:3]=1[O:34][CH3:35].C(N(CC)CC)C.CN(C)C=O.[C:48](Cl)(=[O:50])[CH3:49]>C(Cl)Cl.O>[C:48]([O:1][C:2]1[C:3]([O:34][CH3:35])=[CH:4][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:6][C:7]=1[O:8][CH3:9])(=[O:50])[CH3:49]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10412674HCID 10412674, compound

Product 1

HCID 10506075HCID 10506075, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[2-{5-(4-hydroxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (2.0 g), triethylamine (2.9 ml) and dry N,N-dimethylformamide (20 ml) was added slowly a solution of acetylchloride (0.5 g) in methylene chloride (1.0 ml) at 0° to 5° C. After 1 hour, the reaction mixture was poured into water (200 ml) and stirred for 1 hour. The resulting precipitate was collected, washed with water and air-dried at ambient temperature. The precipitate was subjected to column chromatography on silica gel (60 g) and eluted with a mixture of chloroform and methanol (20:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give pale yellow crystals of 1-[2-{5-(4-acetoxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (1.35 g).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customair-dried at ambient temperature
  4. washeluted with a mixture of chloroform and methanol (20:1 V/V)
  5. additionThe fractions containing the object compound
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b7b7138c81cd4eb1ab4d859b9863f078
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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