Hydrochloric Acid → 5-Chloro-1H-indole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

HRID 651088Notes

Reaction equation

HRID 651088 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][CH2:21][C:22](O)=[O:23])=[O:19])=[CH:12]2.CN(C)C=O.ClCCl.Cl>C(OCC)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:22](=[O:23])[CH2:21][NH:20][C:18]([C:13]2[NH:14][C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=3)=[O:19])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79341Piperidin-4-olHCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycineHCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 155210155-Chloro-1H-indole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxypiperidine (0.83 mmol) and [(5-chloro-1H-indole-2-carbonyl)-amino]-acetic acid (0.8 mmol) were coupled according to procedure A (dimethylformamide-dichloromethane reaction solvent) with the following workup: the reaction mixture was stirred with ethyl acetate and aqueous 2 N HCl, the resulting suspension filtered and the collected solid washed successively with aqueous 2 N HCl, aqueous 2 N NaOH, ether and dried: Yield 180 mg, 68%; TSPMS 336/338 (MH+, 100%);

Workup

  1. filtrationthe resulting suspension filtered
  2. washthe collected solid washed successively with aqueous 2 N HCl, aqueous 2 N NaOH, ether
  3. customdried

Sources & evidence

ORD record
ord-c6474ee2177d4db09776de9db42e7ed9
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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