Methanol → HCID 58780687, compound

HRID 1376027Notes

Reaction equation

HRID 1376027 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22](=O)[NH2:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH2:22][NH2:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 58786549HCID 58786549, compound

Product 1

HCID 58780687HCID 58780687, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4-[Carbamoyl-(2-chloro-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester 462(0.45 g, 1.27 mmol) in THF (10 mL) at 0° C. was added 1.0M BH3 in THF (5.1 mL). The reaction was allowed to stir at reflux for 18 h. MeOH (5.0 mL) was added to the reaction mixture and mixture was then concentrated to dryness. The resulting residue was taken up in MeOH (10 mL) and allowed to reflux for 1 h. The reaction mixture was concentrated to dryness and the resulting residue was taken up in EtOAc (30 mL) and washed with sat. NaHCO3 (30 mL) and brine (30 mL). The organic phase was concentrated to dryness yielding 0.18 g (43%) product.

Workup

  1. temperatureat reflux for 18 h
  2. concentrationwas then concentrated to dryness
  3. temperatureto reflux for 1 h
  4. concentrationThe reaction mixture was concentrated to dryness
  5. washwashed with sat. NaHCO3 (30 mL) and brine (30 mL)
  6. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-70ef63e5bd324babaa1472f99387426c
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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