Dimethylamine → HCID 67545518、化合物

HRID 516370

反応式

HRID 516370 の反応式
O[CH2:2][CH2:3][CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+].[Cl:25][CH2:26][S:27](Cl)(=[O:29])=[O:28].[CH3:31][NH:32][CH3:33]>C(Cl)Cl.C(Cl)Cl.CO>[Cl:25][CH2:26][S:27]([N:5]([CH2:4][CH2:3][CH2:2][N:32]([CH3:33])[CH3:31])[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=[O:29])=[O:28]

参加物

7

反応物 4

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 77054(Chloromethyl)sulfonyl chlorideHCID 43652169tert-Butyl 4-(3-hydroxypropylamino)piperidine-1-carboxylate

生成物 1

HCID 67545518HCID 67545518、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
20 °C

実験手順

To a mixture of tert-butyl 4-[(3-hydroxypropyl)amino]piperidine-1-carboxylate (Yokoyama et al., Bioorg. Med. Chem. 2008, 16, 7968) (710 mg, 2.75 mmol) and dry powdered K2CO3 (5.0 g, 36.0 mmol) in CH2Cl2 (20 mL) at 0° C. was added chloromethanesulfonyl chloride (1 mL, excess). The reaction mixture was stirred at 20° C. for 4 hrs, a solution of 40% aqueous dimethylamine (5 mL) was then added, and stirring was continued for a further 20 hrs. The organic layer was separated and the aqueous layer was further extracted with CH2Cl2 (2×20 mL). The combined organic fractions were washed with water (50 mL) and dried (Na2SO4). The solvent was removed to give an oily product. Chromatography on neutral alumina eluting with CH2Cl2/MeOH (98:2) gave tert-butyl 4-{[(chloromethyl)sulfonyl][3-(dimethylamino)propyl]amino}-1-piperidinecarboxylate, as an oil (946 mg, 87%): 1H NMR (CDCl3) δ 4.47 (s, 2H), 4.22 (br, 2H), 3.82-3.75 (m, 1H), 3.31-3.27 (m, 2H), 2.28-2.46 (m, 2H), 2.76-2.70 (m, 2H), 2.26 (t, J=6.9 Hz, 2H), 2.23 (s, 6H), 1.87-1.64 (m, 6H), 1.46 (s, 9H).

後処理

  1. stirringstirring
  2. waitwas continued for a further 20 hrs
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with CH2Cl2 (2×20 mL)
  5. washThe combined organic fractions were washed with water (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed
  8. customto give an oily product

出典と根拠

ORDレコード
ord-1337e818639c4c16a39c1fc25935430c
出典データセット
uspto-grants-2015_08
特許番号
US09108980B2

関連ノート

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