4-Cyanobenzoyl chloride → HCID 63234702, compound

HRID 717067Notes

Reaction equation

HRID 717067 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:12][NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:13]([CH3:12])[CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 801724-Cyanobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 16640587N-Methyl-1-(1-methylpiperidin-4-yl)methanamine

Product 1

HCID 63234702HCID 63234702, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-cyanobenzoylchloride (200 mg, 1.21 mmol) was dissolved in anhydrous CH2Cl2 (4 mL) and cooled to 0° C. Methyl-(1-methyl-piperidin-4-ylmethyl)-amine (172 mg, 1.21 mmol) in anhydrous CH2Cl2 (1 mL) was added followed by N,N-diisopropylethylamine (0.63 mL, 3.62 mmol). The reaction mixture was allowed to warm to RT over 2 h. The reaction mixture was concentrated in vacuo and the crude product purified by reverse phase preparative HPLC-MS to obtain 4-cyano-N-methyl-N-(1-methyl-piperidin-4-ylmethyl)-benzamide as an off-white solid (213 mg, 65%).

Workup

  1. temperatureto warm to RT over 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-d4b238944fde4ddda437ec0e48fd556d
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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