1-Naphthalenecarbonyl chloride → N-(1-Cyclohexylpyrrolidin-3-yl)naphthalene-1-carboxamide

HRID 441406

反応式

HRID 441406 の反応式
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.[C:13]1([C:23](Cl)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:23]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[O:24])[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

4

反応物 2

HCID 701461-Naphthalenecarbonyl chlorideHCID 36700741-Cyclohexylpyrrolidin-3-amine

生成物 1

HCID 20355413N-(1-Cyclohexylpyrrolidin-3-yl)naphthalene-1-carboxamide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To 9.69 gm. (0.06 mole) of 3-amino-1-cyclohexylpyrrolidine in 50 ml. of chloroform was added dropwise a solution of 8.4 gm. (0.046 mole) of 1-naphthalenecarbonyl chloride in 50 ml. of chloroform. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid. The separated acid layer was made basic with dilute sodium hydroxide solution and extracted with chloroform. The chloroform solution was dried over sodium sulfate, concentrated and the residue crystallized from ethyl acetate. The product weighed 3.8 gm. (25%) and melted at 119°-120° C.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-253b230cbab94e62a5910048b266647d
出典データセット
uspto-grants-1977_08
特許番号
US04039678

関連ノート

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