Triethylamine → HCID 57550245, compound

HRID 548640Notes

Reaction equation

HRID 548640 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH:23]3[CH3:27])=[CH:14][CH:13]=2)[C:9](=[O:28])[CH2:8]1.C(N(CC)CC)C>ClCCl>[Cl:3][CH2:6][CH:7]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH:23]3[CH3:27])=[CH:14][CH:13]=2)[C:9](=[O:28])[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 16662660HCID 16662660, compound

Product 1

HCID 57550245HCID 57550245, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.24 ml, 3.25 mmol, 1.5 eq) is added into a cold solution of 4-(hydroxymethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 72 (0.78 g, 2.16 mmol, 1 eq) and triethylamine (0.3 ml, 2.16 mmol, 1 eq) in dichloromethane (30 ml). The mixture is warmed to room temperature and stirred overnight. The solution is washed once with water and once with a saturated solution of aqueous sodium chloride. The organic layer is dried over magnesium sulfate and concentrated under vacuum to give 0.54 g of 4-(chloromethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one a56 as a dark-red oil.

Workup

  1. washThe solution is washed once with water and once with a saturated solution of aqueous sodium chloride
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7bc0bb2c49f74e4e8576112103a09294
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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