Triethylamine → HCID 18357262, compound

HRID 1955387Notes

Reaction equation

HRID 1955387 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]>O1CCCC1.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)propoxy]-phenyl]methanone hydrochloride was dissolved in 100 ml of tetrahydrofuran, 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-butylsulfonyl chloride in 15 ml of tetrahydrofuran 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 methanol and volume reduced in vacuo. The crude product was chromatographed on a silica gel column, eluted with chloroform-methanol (19:1 v/v). The desired fractions were determined by thin layer chromatography, 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 methanol and volume
  3. customThe crude product was chromatographed on a silica gel column
  4. washeluted with chloroform-methanol (19:1 v/v)
  5. customevaporated to a tan oil

Sources & evidence

ORD record
ord-0b4e1d45306e4dbd81cd464bd87bbe0d
Source dataset
uspto-grants-2000_09
Patent number
US06124311

Reaction notes

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