HCID 18423420, compound → HCID 68513160, compound

HRID 1894951Notes

Reaction equation

HRID 1894951 reaction equation
[OH:1][CH:2]([CH3:17])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.[ClH:18].CCOC(C)=O>C(OCC)(=O)C>[ClH:18].[OH:1][CH:2]([CH3:17])[CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 18423420HCID 18423420, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 68513160HCID 68513160, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 233 mg of tert-butyl 4-(2-hydroxy propyl)piperidine-1-carboxylate in 4 mL of ethyl acetate was added 3 mL of 4M HCl/EtOAc, followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure to obtain 4-(2-hydroxypropyl)piperidine hydrochloride. To a solution of the 4-(2-hydroxypropyl)piperidine hydrochloride and 155 mg of indole-2-carboxylic acid in 5 mL of DMF were added 0.15 mL of triethylamine, 190 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 130 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 0.5M aqueous sodium hydroxide solution and saturated brine, 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 solidified using diisopropyl ether to obtain 49 mg of 1-[1-(1H-indol-2-ylcarbonyl)piperidin-4-yl]propan-2-ol as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c9845e0601c47029d9ae7fe71d15a5a
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

Loading…