Hydrochloric Acid → (s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine hydrochloride

HRID 429835Notes

Reaction equation

HRID 429835 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[ClH:27]>CO.C(OCC)C>[ClH:27].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:24])=[O:25])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10927016(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine

Product 1

HCID 20706301(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(S)-N-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (0.913 grams, 2.4 mmole) was dissolved in warm methanol (20 ml). To this solution was added 1.0M hydrogen chloride (2.5 ml) in ethyl ether. The solvent was removed under reduced pressure. The residue was dissolved in warm 2-butanone (3.0 ml). After 15 hours at 22° C., the crystals were collected and dried in vacuo to give (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine hydrochloride (0.99 grams, 99%), m.p. 112-114° C., M+H 381.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in warm 2-butanone (3.0 ml)
  3. customthe crystals were collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-624530ba5d52459caad641c2ffffc846
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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