Triethylamine → N,O-dimethyl-N-(1-trityl-piperidine-4-carbonyl)hydroxylamine

HRID 278571

Reaction equation

HRID 278571 reaction equation
[C:1]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=O)[CH2:22][CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:30][O:31][NH:32][CH3:33].C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl>[CH3:33][N:32]([O:31][CH3:30])[C:26]([CH:23]1[CH2:22][CH2:21][N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:25][CH2:24]1)=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 205201821-Tritylpiperidine-4-carboxylic acid

Product 1

HCID 22628088N,O-dimethyl-N-(1-trityl-piperidine-4-carbonyl)hydroxylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-tritylpiperidine-4-carboxylic acid (7.0 g), O,N-dimethylhydroxylamine hydrochloride (2.0 g) and triethylamine (2.9 ml) in dichloromethane (70 ml) was added WSC (3.97 g), and the mixture was stirred at room temperature for 1 hour and concentrated. To the residue was added ethyl acetate, and the mixture was washed with water, dried (MgSO4) and concentrated. The resulting crystals (6.3 g) were washed with isopropylether.

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added ethyl acetate
  3. washthe mixture was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washThe resulting crystals (6.3 g) were washed with isopropylether

Sources & evidence

ORD record
ord-13e3f414752049a18edaff60a4782d74
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Linked notes

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