Carbon Dioxide → 3-Methyl-4-(4-morpholinyl)-N-[(2R)-1,2,3,4-tetrahydro-8-(4-methyl-1-piperazinyl)-2-naphthalenyl]benzamide

HRID 1954795Notes

Reaction equation

HRID 1954795 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[NH2:32][C@@H:33]1[CH2:42][CH2:41][C:40]2[C:35](=[C:36]([N:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)[CH:37]=[CH:38][CH:39]=2)[CH2:34]1>CN(C)C=O>[CH3:49][N:46]1[CH2:47][CH2:48][N:43]([C:36]2[CH:37]=[CH:38][CH:39]=[C:40]3[C:35]=2[CH2:34][C@H:33]([NH:32][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[C:2]([CH3:1])[CH:3]=2)[CH2:42][CH2:41]3)[CH2:44][CH2:45]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 184757233-Methyl-4-(morpholin-4-yl)benzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 544091833-Methyl-4-(4-morpholinyl)-N-[(2R)-1,2,3,4-tetrahydro-8-(4-methyl-1-piperazinyl)-2-naphthalenyl]benzamideYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of 3-methyl-4-morpholinobenzoic acid (10 mg, 0.51 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1,1'-carbonyldiimidazole (87 mg, 0.54 mmol) and the reaction was heated at 75° C. When the carbon dioxide evolution had ceased (after 30 min), the reaction was cooled to room temperature and a solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at ambient temperature for 15 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/ethanol saturated with NH3 (100:2) as the eluent gave 110 mg (50% yield) of the title compound as white crystals: mp 172-175° C.; [α]21D -47° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 448 (5, M+).

Workup

  1. custom(after 30 min)
  2. temperaturethe reaction was cooled to room temperature
  3. customthe solvent was evaporated in vacuo
  4. customPurification on a silica gel column

Sources & evidence

ORD record
ord-ffa8d4a070164cae8e8043050301a6b9
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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