Diisopropylamine → HCID 69686359, compound

HRID 2228446Notes

Reaction equation

HRID 2228446 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[CH3:20].C(NC(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:19]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:15]2[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:13][CH:14]=2)[CH2:28][CH2:29]1)=[O:23])[CH3:20]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 18469984HCID 18469984, compound

Product 1

HCID 69686359HCID 69686359, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-(4-aminophenyl)-1-(4-fluorophenyl)propan-1-one (1.1 g, 4.52 mmol) (prepared as described in Example 1b),1-ethoxycarbonylpiperazine (2.15 g, 13.57 mmol), and diisopropylamine (6.5 g, 4.98 mmol) in dimethylsulfoxide (10 mL) was heated at 100-110° C. for about 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (150 mL), washed with cold water and brine. The organic layer was separated, dried, and evaporated in vacua. Purification by silica gel chromatography, eluting with 60% ethyl acetate/hexane, gave the title compound, m.p. 106.3-106.7° C. Analysis for C22H27N3O3: Calcd.: C, 69.27; H, 7.13; N, 11.02. Found: C, 69.13; H, 7.04; N, 11.03.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with cold water and brine
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacua
  6. customPurification by silica gel chromatography
  7. washeluting with 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3ae619d5a7af41ff8ced15e3987fce98
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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