Hydrochloric Acid → HCID 69303640, compound

HRID 1927622Notes

Reaction equation

HRID 1927622 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#N)=[CH:16][C:15]=2[F:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1([Mg]Cl)[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH2:30].Cl>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:30])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 53485511tert-Butyl 4-(4-cyano-2-fluorophenyl)piperazine-1-carboxylateHCID 178478989HCID 178478989, compound

Product 1

HCID 69303640HCID 69303640, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of 4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.27 g, 0.87 mmol) in Et2O (10 mL) was treated with cyclopentylmagnesium chloride (1.5 mL, 2 M). The mixture was allowed to slowly reach rt overnight. The reaction was then cooled to 0° C. and water added (10 mL). The pH of the mixture was adjusted to ˜7 with 1 M HCl and was extracted with Et2O and the solvent removed. Purification on SiO2EtOAc/hexanes) provided 0.19 g of the title compound. MS (ESI): mass calcd. for C21H29FN2O3, 376.47. m/z found, 377.5 [M+H]+.

Workup

  1. customwas allowed to slowly reach rt overnight
  2. extractionwas extracted with Et2O
  3. customthe solvent removed
  4. customPurification on SiO2EtOAc/hexanes)

Sources & evidence

ORD record
ord-720e4e6b38e740b6aba1f48a65ccc119
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

Loading…