Ammonia → 1H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide

HRID 397653ノート

反応式

HRID 397653 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]([OH:21])=O)(=[O:12])=[O:11].C([N:24](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]([NH2:24])=[O:21])(=[O:11])=[O:12]

参加物

6

反応物 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 230007441-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxylic acid

生成物 1

HCID 230006771H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

1-(1H-Benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxylic acid (17.5 g) [see Preparation 16] was dissolved in tetrahydrofuran (180 ml) and cooled to −20° C. Triethylamine (10.2 ml) was added to the mixture followed by ethyl chloroformate (5.4 ml). The reaction mixture was stirred for 1 hour at −20° C. and 0.88 aqueous ammonia solution (25 ml) was added. The mixture was then stirred for a further 2 hours at room temperature. The organic solvent was removed under reduced pressure and ethyl acetate added. The organic layer was separated, washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure to afford 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxamide (14.73 g).

後処理

  1. stirringThe mixture was then stirred for a further 2 hours at room temperature
  2. customThe organic solvent was removed under reduced pressure and ethyl acetate
  3. additionadded
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-e011619fff344d58b0bd4504e7c11e76
出典データセット
uspto-grants-2003_08
特許番号
US06610707B1

反応ノート

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