Triethylamine → 4-(Benzoylamino)-N-[2-(N,N-dimethylamino)methyl-6-tetralinyl]benzamide

HRID 1242931Notes

Reaction equation

HRID 1242931 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][N:14]([CH3:16])[CH3:15])[CH2:7][CH2:6]2.[C:17]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.C1COCC1.O.CN(C=O)C>[C:17]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH2:9][CH:8]([CH2:13][N:14]([CH3:16])[CH3:15])[CH2:7][CH2:6]3)=[O:31])=[CH:33][CH:34]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2525974-(Benzoylamino)benzoic acidHCID 219397736-Amino-2-(N,N-dimethylamino)methyltetralin hydrochloride

Product 1

HCID 219397304-(Benzoylamino)-N-[2-(N,N-dimethylamino)methyl-6-tetralinyl]benzamideYield 84.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

6-Amino-2-(N,N-dimethylamino)methyltetralin hydrochloride (139 mg), 4-benzoylaminobenzoic acid (121 mg), WSCD (0.13 ml), HOBt (92 mg), triethylamine (0.14 ml) and DMAP (61 mg) were added to DMF (4 ml). After the reaction mixture was shaken at room temperature for 20 hours using a shaker, the reaction mixture was poured into water, and extraction was conducted using ethyl acetate-THF (1:1). The organic layer was washed with water, saturated sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried, and then concentrated. The resulting crude crystal was washed with hexane, to give the titled compound (181 mg).

Workup

  1. washThe organic layer was washed with water, saturated sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. washThe resulting crude crystal was washed with hexane

Sources & evidence

ORD record
ord-86da2f95597a466a86901b039b379cdf
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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