4-Amino-1-Boc-piperidine → HCID 23401055, compound

HRID 750753Notes

Reaction equation

HRID 750753 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>CN(C=O)C>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10](=[O:11])[NH2:12])=[CH:8][CH:7]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 122382474-Oxiranylmethoxy-benzamide

Product 1

HCID 23401055HCID 23401055, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Oxiranylmethoxy-benzamide (76 mg, 0.393 mmol) was dissolved in 8 mL of dry DMF, followed by the addition of 4-amino-1-N-boc-piperidine (178 mg, 0.889 mmol). The reaction mixture was stirred at 80° C. for 48 h. The reaction mixture was concentrated and the residue was purified by flash chromatography eluting with 0-5% 2M NH3 in MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 62 mg of 4-[3-(4-carbamoyl-phenoxy)-2-hydroxy-propylamino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluting with 0-5% 2M NH3 in MeOH/CH2Cl2
  4. customThe product fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09840e10d3bb473caa5f858a7213551b
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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