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

HRID 429834Notes

Reaction equation

HRID 429834 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([NH:13][CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:30][S:31]([N:34]1[CH2:39][CH2:38][CH:37]([CH:40]=O)[CH2:36][CH2:35]1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:40][CH:37]3[CH2:38][CH2:39][N:34]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:35][CH2:36]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 109543721-(Methylsulfonyl)piperidine-4-carbaldehydeHCID 11106515(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine

Product 1

HCID 10927016(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amineYield 63%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine (24 grams, 0.117 mole) was dissolved in dichloroethane (300 ml) and sodium triacetoxyborohydride (37.2 grams, 0.176 mole) was added. After stirring for 5 minutes N-methanesulfonylpiperidine-4-carboxaldehyde (22.4 grams, 0.117 mole) was added and the mixture was stirred for another 2 hours. 5% sodium carbonate (600 ml) was added and the mixture was extracted with dichloromethane. Evaporation of the solvent gave an oil which was recrystallized from ether to give (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (28 grams, 63%), m.p. 99-101° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. customEvaporation of the solvent
  4. customgave an oil which
  5. customwas recrystallized from ether

Sources & evidence

ORD record
ord-7add86e5c1a845d4abb08781c75eeb3f
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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