Hydrochloric Acid → N-(2-(5-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)acetamide

HRID 2170864Notes

Reaction equation

HRID 2170864 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][CH2:25][NH:26][C:27](=[O:33])OC(C)(C)C)[CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=O)C.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][CH2:25][NH:26][C:27](=[O:33])[CH3:36])[CH:19]=[CH:18]4)=[O:14])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 86670543tert-Butyl (2-(5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)carbamate

Product 1

HCID 67168200N-(2-(5-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)acetamideYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (1-(2-aminoethyl)-1H-indol-5-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanone (30 mg, 0.075 mmol, Example 385) and pyridine (1 mL) was added acetic anhydride (0.0085 mL, 0.090 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture was poured into 1M aqueous hydrochloric acid solution (5 mL). This was extracted with ethyl acetate (5 mL) and washed with saturated sodium hydrogen carbonate aqueous solution (5 mL) and brine (5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 8.9 mg (27% yield) of the title compound.

Workup

  1. extractionThis was extracted with ethyl acetate (5 mL)
  2. washwashed with saturated sodium hydrogen carbonate aqueous solution (5 mL) and brine (5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-cf31638a8de3473fa49c2a3da28d818f
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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