1-Hydroxybenzotriazole → HCID 21996474, compound

HRID 1978017Notes

Reaction equation

HRID 1978017 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1.[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(OCC)(=O)C.C(OC(C)C)(C)C>CN(C=O)C.O>[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([C:31]([NH:1][CH2:2][CH2:3][CH:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=3)[CH2:6][CH2:5]2)=[O:32])[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110196681-(2-Aminoethyl)-6-methoxyindanHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 21996474HCID 21996474, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-aminoethyl)-6-methoxyindan (1.00 g, 5.23 mmol), 1-benzyloxycarbonyl-4-piperidinecarboxylic acid (1.38 g, 5.23 mmol) and 1-hydroxy-1H-benzotriazole (0.78 g, 5.75 mmol) in DMF (20 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC; 1.10 g, 5.75 mmol). The mixture was stirred for 6 hours at room temperature. To the reaction mixture was added water, and the mixture was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (chloroform/methanol, 95:5) to give 2.10 g (yield 92%) of the above-titled compound, m.p.132-133° C. (recrystallized from ethyl acetate/isopropyl ether).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with brine, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (chloroform/methanol, 95:5)
  6. customto give

Sources & evidence

ORD record
ord-577ea88e9c5a430d85fdf3dc79ce426d
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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