Triethylamine → (s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine

HRID 429837Notes

Reaction equation

HRID 429837 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11](Cl)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].Cl.[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH2:24][C@@H:25]([NH:27][CH2:28][CH3:29])[CH3:26])=[CH:23][C:18]=2[CH2:17][CH2:16]1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH2:24][C@@H:25]([N:27]([C:11]([CH:8]3[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]3)=[O:12])[CH2:28][CH3:29])[CH3:26])=[CH:23][C:18]=2[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 121159931-Methanesulfonylpiperidine-4-carbonyl chlorideHCID 20706299(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamine hydrochloride

Product 1

HCID 20706300(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-methanesulfonylpiperidine-4-carbonyl chloride in dichloromethane (10 ml) was added to a suspension of (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamine hydrochloride (1.21 grams, 5 mmole) in dichloromethane (10 ml). The mixture was cooled to 0° C., and triethylamine (1.7 ml, 12.2 mmol) was added dropwise. When the addition was complete, the mixture was warmed to room temperature and stirred for about 1 hour. Saturated ammonium chloride was added (20 ml) and the separated organic layer was extracted once with dichloromethane (20 ml). The combined organic layers were washed with 1N hydrochloric acid (25 ml), saturated sodium bicarbonate (25 ml), dried over magnesium sulfate, and concentrated to give (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine as an off white foam (2.21 g).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was warmed to room temperature
  3. extractionthe separated organic layer was extracted once with dichloromethane (20 ml)
  4. washThe combined organic layers were washed with 1N hydrochloric acid (25 ml), saturated sodium bicarbonate (25 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b110dfd4584433d9544c49d2bcddbb2
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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