N,O-Dimethylhydroxylamine → Tert butyl 4-(4-(methoxy(methyl)carbamoyl)phenyl)piperidine-1-carboxylate

HRID 2366478Notes

Reaction equation

HRID 2366478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][NH:24][O:25][CH3:26].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1>[CH3:26][O:25][N:24]([CH3:23])[C:18]([C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[CH:22][CH:21]=1)=[O:19]

Participants

6

Reactant 4

HCID 14232N,O-Dimethylhydroxylamine2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86613864Tert butyl 4-(4-(methoxy(methyl)carbamoyl)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid (0.7 g, 2.3 mmol), N,O-dimethylhydroxylamine (0.27 g, 2.8 mmol), 1-hydroxybenzotriazole (0.37 g, 2.7 mmol) and 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (1.1 g, 5.8 mmol) in tetrahydrofuran (15 mL) was stirred at ambient temperature for 48 hours. Additional N,O-dimethylhydroxylamine (0.14 g, 1 mmol) was added and the mixture stirred an additional 4 hours and concentrated. The residue was dissolved in ethyl acetate, washed with water and filtered through silica gel. The solution was concentrated and used without further purification.

Workup

  1. stirringthe mixture stirred an additional 4 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. filtrationfiltered through silica gel
  6. concentrationThe solution was concentrated
  7. customused without further purification

Sources & evidence

ORD record
ord-a612d972c9f145c0ae89b7740754225d
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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