Water → 1,1-Dimethylethyl 3-(methyloxy)-4-[(phenylcarbonyl)amino]-1-piperidinecarboxylate

HRID 2168197Notes

Reaction equation

HRID 2168197 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[O:15][CH3:16].C(N(CC)CC)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C(Cl)Cl>[CH3:16][O:15][CH:3]1[CH:2]([NH:1][C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:31])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53396191tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylate

Product 1

HCID 679880741,1-Dimethylethyl 3-(methyloxy)-4-[(phenylcarbonyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-amino-3-(methyloxy)-1-piperidinecarboxylate D19 (2.85 g) in DCM (100 ml) was added triethylamine (5.2 ml, 37.2 mmol), and benzoyl chloride (2.2 ml, 18.6 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 hours. The resulting mixture was poured into water and extracted with DCM. The organic layer was dried over anhydrous MgSO4, concentrated in vacuo to get the desired product D20 as an oil in 4.0 g. LCMS [MH+] [email protected] and 1.61 min (isomers seen) (5 min run)

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0c6be3021004b64ae049f863fa630a1
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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