Morpholine → 4-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 13555Notes

Reaction equation

HRID 13555 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 59218188Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate

Product 1

HCID 592181854-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(4-formyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (2.06 g) in methanol (100 mL) was treated with morpholine (4 mL) and NaBH(OAc)3 (6.98 g, in portions over 1 h). After 3 h, the mixture was diluted with saturated aquoues NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to yield the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-1c9e992880454582bf5e5259fa550ec0
Source dataset
uspto-grants-2010_06
Patent number
US07728129B2

Reaction notes

Loading…