Dimethylformamide → HCID 9806224, compound

HRID 2304569Notes

Reaction equation

HRID 2304569 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCC[N:19]1[C:23]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:22](=[O:38])[NH:21][C:20]1=[O:39].C(N([CH2:45][CH3:46])CC)C.[CH3:47]N(C)C=O>C(OCC)(=O)C>[C:1]1([C:7]2([C:13]#[N:14])[CH2:8][CH2:9][N:10]([CH2:47][CH2:45][CH2:46][N:21]3[C:22](=[O:38])[C:23]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)[NH:19][C:20]3=[O:39])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1811384-Piperidinecarbonitrile, 4-phenyl-HCID 70157392HCID 70157392, compound

Product 1

HCID 9806224HCID 9806224, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-phenyl-4-cyanopiperidine (328 mg, 1.76 mmol) and 3-bromopropyl-5,5-bis(4-methylphenyl)-imidazolin-2,4-dione (603 mg, 1.5 mmol) in dry dimethylformamide (3 mL) containing triethyl amine (0.28 mL, 2.0 mmol) was warmed at 50° C. for four hours. The cooled reaction mixture was diluted with ethyl acetate. This solution was washed with aq. Na2CO3, water (3×), and then dried over anhydrous Na2SO4,filtered through a pad of charcoal and the solvent evaporated. The residue was triturated with methanol to give pure crystalline product. m.p.: 157-159° C.

Workup

  1. customThe cooled reaction mixture
  2. washThis solution was washed with aq. Na2CO3, water (3×)
  3. dry with materialdried over anhydrous Na2SO4,filtered through a pad of charcoal
  4. customthe solvent evaporated
  5. customThe residue was triturated with methanol
  6. customto give pure crystalline product

Sources & evidence

ORD record
ord-c119d6425a5645fcaafe70b0f75c3200
Source dataset
uspto-grants-2002_08
Patent number
US06436962B1

Reaction notes

Loading…