Water → 4-chloro-N-(1-methylcyclohexyl)butanamide

HRID 2235224Notes

Reaction equation

HRID 2235224 reaction equation
[CH3:1][C:2]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCN(CC)CC.[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21].O>C1COCC1>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([NH:8][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 30215781-Amino-1-methylcyclohexane

Product 1

HCID 633083354-chloro-N-(1-methylcyclohexyl)butanamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-methylcyclohexanamine (0.78 g, 6.89 mmol) in anhydrous THF (100 mL) and cool to 0° C. Add Et3N (3.49 g, 34.45 mmol) and 4-chlorobutanoyl chloride (1.94 g, 13.78 mmol) with stirring under N2. Stir the reaction mixture for 2 hours at room temperature and add water (100 mL). Extract the aqueous with EtOAc (3×200 mL) and then combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 30-80% of EtOAc-Hexane) to give 1.35 g (90%) of 4-chloro-N-(1-methylcyclohexyl)butanamide as a colorless oil.

Workup

  1. extractionExtract the aqueous with EtOAc (3×200 mL)
  2. dry with materialdry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 30-80% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-8052b365b29d47b8bcb3b3fa9ceb8112
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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