Aniline → HCID 21939966, compound

HRID 1242871Notes

Reaction equation

HRID 1242871 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O-])=[O:26])=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)(C)C(Cl)=O.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(=O)(O)[O-].[Na+]>C1COCC1.C(N(CC)CC)C>[C:38]1([NH:37][C:25](=[O:26])[C:24]2[CH:23]=[CH:22][C:21]([CH2:20][O:19][C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[CH2:10][CH:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:18][CH2:17]4)=[CH:29][CH:28]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 21939875HCID 21939875, compound

Product 1

HCID 21939966HCID 21939966, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

Triethylamine (0.11 ml) was added to THF suspension (3 ml) of 4-[[2-(2-piperidinoethyl)-6-tetralinyl]oxymethyl]benzoate (300 mg). Further, THF solution (0.5 ml) of trimethylacetyl chloride (92 mg) was added dropwise under ice-cooling, which was stirred for 30 minutes. The temperature of the reaction mixture was raised to room temperature, which was stirred for 1 hour. THF solution (0.5 ml) of aniline (85 mg) was added dropwise to the reaction mixture under ice-cooling, which was stirred for 1 hour. After the reaction mixture was stirred for 24 hours at room temperature, saturated sodium bicarbonate solution was added, and extraction was conducted using a mixed solution of ethyl acetate and THF. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was recrystallized from THF-methanol-IPE to give the titled compound (150 mg).

Workup

  1. temperaturecooling
  2. stirringwhich was stirred for 1 hour
  3. temperaturecooling
  4. stirringwhich was stirred for 1 hour
  5. stirringAfter the reaction mixture was stirred for 24 hours at room temperature
  6. extractionextraction
  7. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was recrystallized from THF-methanol-IPE

Sources & evidence

ORD record
ord-01afb90724e245e39bf47801de9e4df6
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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