Potassium Carbonate → n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-(4-ethylpiperazin-1-yl)propanamide, dihydrochloride

HRID 916354Notes

Reaction equation

HRID 916354 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([NH:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]#[N:26])=[CH:17][CH:16]=3)[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].[CH2:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[ClH:1].[ClH:1].[C:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([N:14]2[CH:12]3[CH2:11][CH2:10][CH:9]2[CH2:8][CH:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:2][N:32]2[CH2:33][CH2:34][N:29]([CH2:27][CH3:28])[CH2:30][CH2:31]2)[CH2:13]3)=[CH:16][CH:17]=1)#[N:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 692265953-Chloro-N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide

Product 1

HCID 131726601n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-(4-ethylpiperazin-1-yl)propanamide, dihydrochlorideYield 79.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

165RL50 (65 mg, 0.18 mmol), 1-ethylpiperazine (45 μL, 0.35 mmol) and potassium carbonate (49 mg, 0.35 mmol) were stirred in acetonitrile (6 mL) at 50° C. for 2 days. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with water (2×10 mL). The organic solution was dried over sodium sulfate, filtered and evaporated. The product was purified by column chromatography using ethyl acetate/MeOH (9:1) to give the title compound (37 mg, 46%) pure product.

Workup

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-0352705960934f72b9171493bbd808b8
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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