1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 66920127, compound

HRID 1908629Notes

Reaction equation

HRID 1908629 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.CN1CCOCC1.[F:54][C:55]([F:69])([F:68])[C:56]1[CH:57]=[C:58]([N:62]2[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]2)[CH:59]=[CH:60][CH:61]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:10](=[O:12])[N:65]1[CH2:64][CH2:63][N:62]([C:58]2[CH:59]=[CH:60][CH:61]=[C:56]([C:55]([F:68])([F:69])[F:54])[CH:57]=2)[CH2:67][CH2:66]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 79724-MethylmorpholineHCID 1074725-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 66920127HCID 66920127, compoundYield 170.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.53 g of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester and 2.46 g of TOTU was dissolved in 15 ml of DMF. The, 3.29 ml of N-Methylmorpholine was added and the mixture was stirred for 30 min at RT. 1.72 g of 1-(3-Trifluoromethyl-phenyl)-piperazine was added and stirring was continued for 5 h. The mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate solution. Drying of the organic phase over sodium sulfate and evaporation of the solvents under reduced pressure afforded a brownish powder that was purified by chromatography over silica gel eluting with ethyl acetate/heptane 1:2 to 100% ethyl acetate to give 7 g of the desired product.

Workup

  1. stirringstirring
  2. waitwas continued for 5 h
  3. washwashed with saturated sodium hydrogen carbonate solution
  4. dry with materialDrying of the organic phase over sodium sulfate and evaporation of the solvents under reduced pressure
  5. customafforded a brownish powder that
  6. customwas purified by chromatography over silica gel eluting with ethyl acetate/heptane 1

Sources & evidence

ORD record
ord-ccd296bcf2ec460e951fe4394e10abd8
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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