Potassium Carbonate → HCID 57442428, compound

HRID 2262704Notes

Reaction equation

HRID 2262704 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:11]1([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)[CH2:6][CH2:7]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27579714-(4'-Cyanophenyl)piperidineHCID 57442325HCID 57442325, compound

Product 1

HCID 57442428HCID 57442428, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-1-(4-cyclopentyl-piperazin-1-yl)-ethanone (1.2 mmol), 4-piperidin-4-yl-benzonitrile (1.2 mmol) and potassium carbonate (2.4 mmol) in acetonitrile (10 mL) is stirred at rt overnight. The solvent is removed in vacuo and to the residue is added DCM (40 mL) and aqueous sodium bicarbonate (15 mL). The layers are separated and aqueous layer is extracted with DCM (15 mL). The combined organic layers are dried (MgSO4) and solvent removed in vacuo to give the crude product, which is purified by PTLC (5% MeOH in DCM) to give the title compound. 1H NMR (CDCl3) δ 7.59 (2H, d), 7.32 (2H, d), 3.64 (4H, br,), 3.22 (2H, s), 3.01 (2H, br), 2.40˜2.62 (6H, m), 2.21 (2H, dt), 0.80˜1.95 (12H, m); LC-MS (M+1) 381.

Workup

  1. customThe solvent is removed in vacuo and to the residue
  2. additionis added DCM (40 mL) and aqueous sodium bicarbonate (15 mL)
  3. customThe layers are separated
  4. extractionaqueous layer is extracted with DCM (15 mL)
  5. dry with materialThe combined organic layers are dried (MgSO4) and solvent
  6. customremoved in vacuo
  7. customto give the crude product, which
  8. customis purified by PTLC (5% MeOH in DCM)

Sources & evidence

ORD record
ord-6e03889d2cb446a08893d7ec403daab1
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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