Water → HCID 15072973, compound

HRID 2082341Notes

Reaction equation

HRID 2082341 reaction equation
[C:1](Cl)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:16]([O:20][C:21]([NH:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O>C(Cl)Cl>[C:16]([O:20][C:21]([NH:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[C:1](=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 87288Tridecanoyl chlorideHCID 2756031tert-butyl N-((piperidin-2-yl)methyl)carbamate

Product 1

HCID 15072973HCID 15072973, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of 14.3 grams (61.4 mmol) of tridecanoyl chloride in 50 mL of methylene chloride was added 7.49 grams (61.3 mmol) of N,N-dimethylaminopyridine. The resulting suspension was stirred for 10 minutes and then 11.0 grams (51.3 mmol) of 2-[N-(tert-butoxycarbonyl)aminomethyl]piperidine in 50 mL of methylene chloride was added. The mixture was allowed to warm to room temperature while stirring overnight and poured into water. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with brine and dried over MgSO4. Solvent was removed at reduced pressure and the crude product was chromatographed on 250 grams of silica gel eluting with 25% ethyl acetate in hexane to provide 20.9 grams (99%) of N-(tert-butoxycarbonyl)-N-([1-(1-oxotridecyl)-2-piperidinyl]methyl)amine as a viscous orange oil.

Workup

  1. stirringwhile stirring overnight
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customSolvent was removed at reduced pressure
  6. customthe crude product was chromatographed on 250 grams of silica gel eluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-45d8e7f0b27246088daa75dfd97c0af3
Source dataset
uspto-grants-1993_02
Patent number
US05189046

Reaction notes

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