Triethylamine → tert-Butyl 4-{[2-(ethoxyacetyl)hydrazino]carbonyl}piperidine-1-carboxylate

HRID 419850

Reaction equation

HRID 419850 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][CH2:21][C:22](O)=[O:23])[CH3:19].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH2:18]([O:20][CH2:21][C:22]([NH:17][NH:16][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)=[O:15])=[O:23])[CH3:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12301Ethoxyacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 59347451tert-Butyl 4-{[2-(ethoxyacetyl)hydrazino]carbonyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (WO 2000039125, prep 27) (3 g, 12.33 mmol), ethoxyacetic acid (1.28 mL, 13.56 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.6 g, 13.56 mmol), 1-hydroxybenzotriazole hydrate (1.83 g, 13.56 mmol) and triethylamine (2.1 mL, 14.8 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and aqueous sodium carbonate solution. The layers were separated, the organic phase was dried over MgSO4 and evaporated under reduced pressure to provide the title compound as an oil, that crystallised on standing.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium carbonate solution
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-550260baae444d04aaa2bb4b4d2ba678
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Linked notes

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