Water → HCID 178468906, compound

HRID 906179Notes

Reaction equation

HRID 906179 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[C:20]#[N:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br.O>CN(C)C=O>[C:20]([C:19]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=1[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([N:1]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:3][CH2:4]1)#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178468907HCID 178468907, compound

Product 1

HCID 178468906HCID 178468906, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 3-[(trans-4-aminocyclohexyl)amino]-4-cyanobenzoate (0.490 g, 0.96 mmol), potassium carbonate (0.66 g, 4.78 mmol) and 1,5 dibromopentane (0.130 mL, 0.96 mmol) was stirred in dimethylformamide (10 mL) at room temperature for 48 h. Water (20 mL) was then added to the mixture, and the water phase was extracted with dichloromethane (2×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using methanol in dichloromethane (5% to 10%) to afford ethyl 4-cyano-3-[(trans-4-piperidin-1-ylcyclohexyl)amino]benzoate (0.145 g, 43% yield). MS (EI) for C21H29N3O2: 356 (MH+).

Workup

  1. extractionthe water phase was extracted with dichloromethane (2×30 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c7640cacd714c488b7eb4e3d9b0d478
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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