Sodium Hydroxide → Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate

HRID 492910Notes

Reaction equation

HRID 492910 reaction equation
Cl.CN(C(C)C(O)=[O:7])C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])C.[C:32]([O:36][C:37]([NH:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][C:26]([N:43]1[CH2:42][CH2:41][CH:40]([NH:39][C:37](=[O:38])[O:36][C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:45][CH2:44]1)=[O:7]

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7238334-(N-Boc-amino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 216146742-Dimethylamino-propionic acid hydrochloride

Product 1

HCID 57677405Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamateYield 104.2%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals.

Workup

  1. stirringstirred
  2. waitat room temperature for 30 minutes
  3. customthe mixture was partitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with 1N aqueous sodium hydroxide and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e51d5ec59e544627914ced4de06827d2
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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