Piperidine → 3-piperidin-1-yl-propane-1-sulfonic acid {3-[4-(6-phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acryloyl}-amide

HRID 2253483Notes

Reaction equation

HRID 2253483 reaction equation
[C:1]1([C:7]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([NH:28][S:29]([CH2:32][CH2:33][CH2:34]Cl)(=[O:31])=[O:30])=[O:27])=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1>[C:1]1([C:7]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([NH:28][S:29]([CH2:32][CH2:33][CH2:34][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)(=[O:31])=[O:30])=[O:27])=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 866014713-chloro-propane-1-sulfonic acid {3-[4-(6-phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acryloyl}-amide

Product 1

HCID 866014723-piperidin-1-yl-propane-1-sulfonic acid {3-[4-(6-phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acryloyl}-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared by coupling 2i and piperidine (15 eq)in tetrahydrofuran at reflux. The product was isolated as the HCL salt. Yield (70%); 1H NMR (d6-DMSO) δ 11.90 (br s, 1H), 7.53 (d, J=15.7 Hz, 1H), 7.34-7.10 (m, 12H), 6.88 (d, J=8.4 Hz, 2H), 6.70 (d, J=7.3 Hz, 1H), 6.55 (d, J=15.7 Hz, 1H), 3.52 (t, J=7.3 Hz, 2H), 3.09 (br, 2H), 2.77 (br m, 4H), 2.26 (br t, 2H), 2.08 (br, 4H), 1.71 (br, 5H); APcI m/z: 555 (M+H+).

Workup

  1. customPrepared
  2. temperatureat reflux
  3. customThe product was isolated as the HCL salt
  4. customYield (70%)

Sources & evidence

ORD record
ord-85d695f42c114029ac8212a393f2cee7
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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