Triethylamine → N,N-Diallyl-N-({5-[(4-{3-[(trifluoromethyl)sulfonyl]anilino}piperidin-1-yl)sulfonyl]-thien-2-yl}methyl)amine

HRID 906638Notes

Reaction equation

HRID 906638 reaction equation
[F:1][C:2]([F:20])([F:19])[S:3]([C:6]1[CH:7]=[C:8]([NH:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].CCN(CC)CC.[CH2:28]([N:31]([CH2:35][C:36]1[S:40][C:39]([S:41](Cl)(=[O:43])=[O:42])=[CH:38][CH:37]=1)[CH2:32][CH:33]=[CH2:34])[CH:29]=[CH2:30]>C(Cl)Cl>[CH2:32]([N:31]([CH2:28][CH:29]=[CH2:30])[CH2:35][C:36]1[S:40][C:39]([S:41]([N:16]2[CH2:17][CH2:18][CH:13]([NH:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([C:2]([F:1])([F:19])[F:20])(=[O:5])=[O:4])[CH:7]=3)[CH2:14][CH2:15]2)(=[O:43])=[O:42])=[CH:38][CH:37]=1)[CH:33]=[CH2:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776457N-(3-((trifluoromethyl)sulfonyl)phenyl)piperidin-4-amineHCID 113807695-Diallylaminomethyl-thiophene-2-sulfonyl chloride

Product 1

HCID 86761398N,N-Diallyl-N-({5-[(4-{3-[(trifluoromethyl)sulfonyl]anilino}piperidin-1-yl)sulfonyl]-thien-2-yl}methyl)amineYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-trifluoromethanesulfonyl-phenylamino)-piperidine (731 mg, 237 mmol) and Et3N (0.5 mL, 3.58 mmol) in CH2Cl2 (20 mL) was treated with the diallylamino sulfonyl chloride 269b 23° C. A thick precipitate appeared within 5 min, and the mixture was stirred overnight (even if complete within minutes). Dilution with CH2Cl2 (50 mL), washing (1120; brine), drying (MgSO4), and evaporation afforded the crude product, which was filtered over silica gel (AcOEt:cyclohexane 1:1) to afford 1.15 g (86%) of the title bisallylamine, which was used in the next step without further purification.

Workup

  1. washDilution with CH2Cl2 (50 mL), washing (1120; brine)
  2. customdrying
  3. custom(MgSO4), and evaporation
  4. customafforded the crude product, which
  5. filtrationwas filtered over silica gel (AcOEt:cyclohexane 1:1)

Sources & evidence

ORD record
ord-c77cbc0ec4854d71a1cc11b5f11eb2a0
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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