Chloroacetaldehyde → 2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 2085649ノート

反応式

HRID 2085649 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].[Cl:23][CH2:24][CH:25]=O.Cl.C([BH3-])#N.[Na+]>CO>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:25][CH2:24][Cl:23])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2)=[O:8]

参加物

6

反応物 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 227314875-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

生成物 1

HCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

5-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (7 g, Example 29b) and chloroacetaldehyde (50% solution in water, 6.6 ml) were stirred in methanol (120 ml) under nitrogen for 10 min. A mixture of 6M hydrochloric acid (1.8 ml) and methanol (1.8 ml) was added, followed by sodium cyanoborohydride (1.48 g). The mixture was stirred for 2.5 h. The methanol was then removed under reduced pressure and the residue partitioned between saturated aqueous sodium hydrogencarbonate and dichloromethane The aqueous layer was extracted twice more with dichloromethane and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the sub-title compound (8.2 g).

後処理

  1. additionwas added
  2. customThe methanol was then removed under reduced pressure
  3. customthe residue partitioned between saturated aqueous sodium hydrogencarbonate and dichloromethane The aqueous layer
  4. extractionwas extracted twice more with dichloromethane
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a4597dfe232b40f3beee887d4a6d3ac5
出典データセット
uspto-grants-2004_04
特許番号
US06720452B2

反応ノート

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