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Hydrochloric Acid → 5-Chloro-2-piperazinyl-n-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide, hydrochloride salt

HRID 497014
ノート
印刷プレビュー

反応式

HRID 497014 の反応式
[Cl:1]C1[CH:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)=[O:9])[C:5]([Cl:22])=[CH:4][N:3]=1.C(O[C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=O)(C)(C)C.Cl>CS(C)=O.CO.O1CCOCC1>[ClH:1].[Cl:22][C:5]1[C:6]([C:8]([NH:10][CH2:11][C:12]23[CH2:13][CH:14]4[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]4)[CH2:19]2)[CH2:21]3)=[O:9])=[CH:7][C:28]([N:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]2)=[N:3][CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 11416492N-(1-adamantylmethyl)-2,5-dichloroisonicotinamide

生成物 1

HCID 102242375-Chloro-2-piperazinyl-n-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide, hydrochloride salt収率 51.8%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒
HCID 887Methanol溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2,5-dichloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide (0.30 g, Example 1a) and 1-t-butoxycarbonylpiperazine (0.344 g) in dimethylsulfoxide (3 ml) was heated at 160° C. for 40 min. The solution was cooled and partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane and the organic layer dried over magnesium sulphate. Concentration in vacuo and chromatography on silica gave a colourless solid. This was redissolved in methanol and treated with 4M HCl in dioxan (4 ml). Once deprotection was complete the solution was partially concentrated in vacuo then diluted slowly with diethyl ether with rapid stirring. The resulting white precipitate was filtered, washed with diethyl ether and dried to afford the title compound (0.195 g).

後処理

  1. temperatureThe solution was cooled
  2. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  3. dry with materialthe organic layer dried over magnesium sulphate
  4. concentrationConcentration in vacuo and chromatography on silica
  5. customgave a colourless solid
  6. concentrationwas partially concentrated in vacuo
  7. additionthen diluted slowly with diethyl ether with rapid stirring
  8. filtrationThe resulting white precipitate was filtered
  9. washwashed with diethyl ether
  10. customdried

出典と根拠

ORDレコード
ord-d9337884d7c74167809713ac9b5a1bcd
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949539B2

反応ノート

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