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Hydrochloric Acid → 1-{1-[(5-chloro-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol

HRID 1894945
Notes
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Reaction equation

HRID 1894945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[CH3:14][C:15]([OH:24])([CH3:23])[CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][C:15]([CH3:23])([OH:24])[CH3:14])[CH2:18][CH2:19]1)=[O:13])=[CH:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184234282-Methyl-1-(piperidin-4-yl)propan-2-ol

Product 1

HCID 25181559
1-{1-[(5-chloro-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol
Yield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 370 mg of 5-chloroindole-2-carboxylic acid and 300 mg of 2-methyl-1-(piperidin-4-yl)-2-propanol in 8 mL of DMF were added 360 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 250 mg of 1-hydroxybenzotriazole, followed by stirring at room temperature for 1 day. 0.5M aqueous hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with 0.5 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1], and then crystallized from diisopropyl ether to obtain 268 mg of 1-{1-[(5-chloro-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol as a white crystal.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 0.5 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1]
  6. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7f5b16ae7c984097b7e24bf329c2eab7
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08513422B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes