Water → 2-[(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)amino]-N-cyclohexyl-N-phenylacetamide

HRID 890506

Reaction equation

[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[CH2:25][C:26]([NH:28][CH:29]1[C:34]([CH3:36])([CH3:35])[CH:33]2[CH2:37][C:30]1([CH3:38])[CH2:31][CH2:32]2)=O.[OH2:39]>O1CCCC1>[CH:8]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:25](=[O:39])[CH2:26][NH:28][CH:29]2[C:34]([CH3:36])([CH3:35])[CH:33]3[CH2:37][C:30]2([CH3:38])[CH2:31][CH2:32]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-cyclohexylaniline (100 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at −78° C. was added LiHMDS (1 ml of a 1M solution in tetrahydrofuran) dropwise. The solution was allowed to warm to 0° C., then recooled to −78° C., and a solution of 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide (124 mg, 0.56 mmol) in tetrahydrofuran (1 ml) added dropwise. The mixture was allowed to warm to room temperature, and was stirred for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The ethyl acetate solution was absorbed onto silica gel, which was eluted with 3% methanol/methylene chloride, to yield N-cyclohexyl-N-phenyl-2-(1,3,3-trimethyl-bicyclo[2.2.1]hept-2-ylamino)-acetamide.

Workup

customrecooled to −78° C.
temperatureto warm to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customThe ethyl acetate solution was absorbed onto silica gel, which
washwas eluted with 3% methanol/methylene chloride

Sources & evidence

ORD record: ord-ac59e46a7a7e4ba19be4a36a44a1572f
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995285B2

Linked notes

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