1-Hydroxybenzotriazole → HCID 57936068, compound

HRID 1434561Notes

Reaction equation

HRID 1434561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH:17][C@H:18]1[CH2:27][C:26]2[C:25]([NH2:28])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:20][CH2:19]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][CH:11]([C:14]([NH:28][C:25]3[C:26]4[CH2:27][C@H:18]([OH:17])[CH2:19][CH2:20][C:21]=4[CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579360781-(3-Chlorophenyl)-4-piperidinecarboxylic acidHCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

Product 1

HCID 57936068HCID 57936068, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

120 mg (0.50 mmol) of 1-(3-chlorophenyl)-piperidine-4-carboxylic acid, 74 mg (0.46 mmol) of (7R)-7-hydroxy-5,6,7,8-tetrahydronaphthaleneamine, 74 mg (0.55 mmol) of 1-hydroxy-1H-benzotriazole and 113 mg (0.59 mmol) of (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were combined in 3 ml of N,N-dimethylformamide under an argon atmosphere and stirred at room temperature overnight. Ethyl acetate was added, the mixture washed with water and the aqueous phase re-extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by RP-BPLC in a water/acetonitrile gradient, yielding 57 mg (33% yield) of 1-[3-chlorophenyl]-N-[(7R)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]piperidine-4-carboxamide.

Workup

  1. washthe mixture washed with water
  2. extractionthe aqueous phase re-extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by RP-BPLC in a water/acetonitrile gradient

Sources & evidence

ORD record
ord-3b93eae5e5ce4e40a4ad501d0e7d4296
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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