Triethylamine → HCID 18357262, compound

HRID 374946Notes

Reaction equation

HRID 374946 reaction equation
Cl.O[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:29]3[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=3)[S:8][C:7]=2[CH:36]=1.C(N([CH2:42][CH3:43])CC)C.[CH2:44]([S:48](Cl)(=[O:50])=[O:49])[CH2:45][CH2:46][CH3:47]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:44]([S:48]([C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:29]3[CH:34]=[CH:33][C:32]([S:48]([CH2:44][CH2:45][CH2:42][CH3:43])(=[O:50])=[O:49])=[CH:31][CH:30]=3)[S:8][C:7]=2[CH:36]=1)(=[O:50])=[O:49])[CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 22001233HCID 22001233, compound

Product 1

HCID 18357262HCID 18357262, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2.5 g (4.77 mmol) of [6-hydroxy-2-[4-hydroxyphenyl]benzo[b]thien-3-yl][4-[3-(1-piperidinyl)propyloxy]phenyl]methanone hydrochloride was dissolved in 100 mL of THF, 3.9 g (39 mmol) of triethylamine and 10 mg of DMAP were added. The reaction mixture was stirred for 15 minutes at room temperature and under a nitrogen blanket. 4 g (25.5 mmol) of n-butylsulfonoyl chloride in 15 mL of THF was slowly added. The reaction was allowed to proceed for eighteen hours at room temperature and under nitrogen. The reaction was quenched with the addition of 25 mL MeOH and volume reduced in vacuo. The crude product was chromatographed on a silica gel column, eluted with CHCl3 --MeOH (19:1 v/v). The desired fractions were determined by TLC, combined, and evaporated to a tan oil.

Workup

  1. waitto proceed for eighteen hours at room temperature and under nitrogen
  2. customThe reaction was quenched with the addition of 25 mL MeOH and volume
  3. customThe crude product was chromatographed on a silica gel column
  4. washeluted with CHCl3 --MeOH (19:1 v/v)
  5. customevaporated to a tan oil

Sources & evidence

ORD record
ord-ab59b964d07142ad859e604cfca120d6
Source dataset
uspto-grants-1996_01
Patent number
US05482949

Reaction notes

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