Sodium Hydroxide → HCID 21487853、化合物

HRID 1414574ノート

反応式

HRID 1414574 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.[BH4-].[Na+].[OH-].[Na+]>C1C=CC=CC=1.CCOCC.O.C(O)(=O)C.C(O)C>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][CH:18]1[CH2:19][CH2:20][N:15]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:16][CH2:17]1

参加物

10

反応物 4

HCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 4311764Sodium borohydrideHCID 147388231-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinone

生成物 1

HCID 21487853HCID 21487853、化合物収率 52.2%

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

1-(6,7-Dimethoxyquinazolin-4-yl)piperid-4-one (2.9g) (which may be prepared as in part A of Example 91, hereinafter), and 2-aminomethylpyridine (1.19g) were refluxed together for two hours in benzene (50 ml.) in a flask fitted with a Dean and Stark trap. Ethanol (50 ml.) was added to the cooled solution followed by the slow addition of sodium borohydride (0.76g) with stirring. On completion of the addition stirring as continued for two hours followed by the addition of excess acetic acid. The mixture was poured into water, basified with 5N sodium hydroxide and was extracted with chloroform. Evaporation of the chloroform layer gave a yellow oil which solidified on trituration with ether. Recrystallization from ethyl acetate gave 4-[4-(2-pyridylmethyl-amino)piperidino]-6,7-dimethoxyquinazoline (2 g) m.p. 151°-155° C.

後処理

  1. customfitted with a Dean and Stark trap
  2. additionOn completion of the addition
  3. stirringstirring
  4. extractionwas extracted with chloroform
  5. customEvaporation of the chloroform layer
  6. customgave a yellow oil which
  7. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-ef547666bb804d20b90fd13fe304d326
出典データセット
uspto-grants-1977_01
特許番号
US04001422

反応ノート

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