Piperidine → 3-Piperidin-1-yl-propane-1-sulfonic acid {3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-amide

HRID 2253471

Reaction equation

HRID 2253471 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:27][S:28]([CH2:31][CH2:32][CH2:33]Cl)(=[O:30])=[O:29])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCCC1>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:27][S:28]([CH2:31][CH2:32][CH2:33][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)(=[O:30])=[O:29])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 866014693-Chloro-propane-1-sulfonic acid {3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-amide

Product 1

HCID 726251473-Piperidin-1-yl-propane-1-sulfonic acid {3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared by coupling 1x and piperidine (15 eq)in tetrahydrofuran at reflux. 1z was then precipitated from a mixture of ethyl acetate and 1N HCl as the HCl salt. Yield (60%); 1H NMR (d6-DMSO) δ 11.90 (br s, 1H), 7.47 (d, J=15.7 Hz, 1H), 7.40-7.09 (m, 12H), 6.87 (d, J=7.7 Hz, 2H), 6.53 (d, J=15.7 Hz, 1H), 3.08 (br, 2H), 2.95 (br, 1H), 2.81 (br, 2H), 2.37 (q, J=7.3 Hz, 2H), 2.08 (br, 2H), 1.71 (br, 6H), 1.62 (br, 1H), 0.83 (t, J=7.3 Hz, 3H); APcI m/z: 541 (M−H−).

Workup

  1. customPrepared
  2. temperatureat reflux
  3. custom1z was then precipitated from a mixture of ethyl acetate and 1N HCl as the HCl salt
  4. customYield (60%)

Sources & evidence

ORD record
ord-2a0e215ed36b43a1be120c03f750b02b
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Linked notes

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