Benzhydrylamine → HCID 22110990, compound

HRID 565661Notes

Reaction equation

HRID 565661 reaction equation
[NH2:1][C:2]1[C:3]([CH3:24])=[C:4]([CH3:23])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O-])=[O:19])[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:21]=1[CH3:22].[Na+].Cl.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[C:44]1([CH:50]([NH2:57])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[NH2:1][C:2]1[C:3]([CH3:24])=[C:4]([CH3:23])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([C:18]([NH:57][CH:50]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:19])[CH2:16][CH2:17]3)([CH3:10])[CH2:7][C:6]=2[C:21]=1[CH3:22]

Participants

8

Reactant 5

HCID 7036BenzhydrylamineHCID 11130Triethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23667828HCID 23667828, compound

Product 1

HCID 22110990HCID 22110990, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium 1-[(5-amino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)methyl]-4-piperidinecarboxylate (0.89 g) in N,N-dimethylformamide (10 mL) was added 0.35 g of triethylamine hydrochloride and the mixture was stirred at room temperature for 5 minutes. To this mixture were added 0.34 g of 1-hydroxybenzotriazole and 0.46 g of 1,1-diphenylmethylamine. Then, under ice-cooling, 0.48 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added. This mixture was stirred under nitrogen gas at room temperature for 23 hours. This reaction mixture was diluted with water and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from methanol/diisopropyl ether to provide 0.71 g of the title compound. Yield 57%.

Workup

  1. temperatureThen, under ice-cooling
  2. stirringThis mixture was stirred under nitrogen gas at room temperature for 23 hours
  3. extractionextracted with 2 portions of ethyl acetate
  4. washThe pooled organic layer was washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-1da96b5c3f294d37b73dc207e7fca655
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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