1,2-Dichloroethane → n-Methyl-n-methoxy-4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-butanamide

HRID 2185570Notes

Reaction equation

HRID 2185570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24].C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[CH3:21][N:22]([O:23][CH3:24])[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 104009874-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)butanoic acid

Product 1

HCID 16743429n-Methyl-n-methoxy-4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-butanamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-butanoic acid (291 mg, 1.07 mmol, from Step A), N,O-dimethylhydroxylamine hydrochloride (177 mg, 1.82 mmol), EDC (350 mg, 1.82 mmol), and triethylamine, 0.25 mL, 1.82 mmol) were stirred together in 5 mL CH2Cl2 for 16 h. The mixture was diluted with 100 mL CH2Cl2 and washed with 1M HCl. The organic layer was dried over MgSO4 and concentrated. Flash chromatography (1/1 hexane/EtOAc) afforded 237 mg (71%) of the title compound.

Workup

  1. washwashed with 1M HCl
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5941454dbcd24fbc85214d95c157175d
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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