Dimethylformamide → HCID 10814826, compound

HRID 2051398Notes

Reaction equation

HRID 2051398 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12]([NH:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:13])=[CH:4][C:3]=1[O:32][CH3:33].CN1CC[O:38][CH2:37][CH2:36]1.CN(C)C=O.C(Cl)(=O)C>O>[C:37]([O:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12]([NH:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:13])=[CH:4][C:3]=1[O:32][CH3:33])(=[O:38])[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 10623224HCID 10623224, compound

Product 1

HCID 10814826HCID 10814826, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-[2-{5-(4-hydroxy-3-methoxyphenyl)(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (0.89 g), dry N-methylmorpholine (1.0 g) and dry N, N-dimethylformamide (10 ml) was added slowly acetyl chloride (0.26 g) at 5° to 10° C. After stirring for 1 hour, the reaction mixture was poured into water (50 ml) and stirred for 1 hour. The resulting precipitate was collected, washed with water and then recrystallized from a mixture of ethanol and water (7:3 V/V) to give 1-[2-{5-(4-acetoxy-3-methoxyphenyl)-(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (0.22 g).

Workup

  1. stirringstirred for 1 hour
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customrecrystallized from a mixture of ethanol and water (7:3 V/V)

Sources & evidence

ORD record
ord-f41803f8d84a4517b8e59422a422033d
Source dataset
uspto-grants-1991_05
Patent number
US05017703

Reaction notes

Loading…