Hydrochloric Acid → 6-Cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

HRID 55335ノート

反応式

HRID 55335 の反応式
C([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[C:13]3[CH2:20][CH:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:22][CH:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.C([Li])CCC.Cl>C1COCC1.CCCCCC>[C:18]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][CH2:10][CH:11]3[CH2:22][CH:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:20][C:13]=1[C:12]=23)#[N:19]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 148320451-Benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indoleHCID 178418339Butyllithium

生成物 1

HCID 148320466-Cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole収率 113.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 4.8 g (0.0124 mol) of (±)-1-benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 mL of THF cooled to -78° C. under a N2 atmosphere were added 16 mL (0.025 mol) of a 1.6 M solution of n-butyl lithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes and then allowed to warm to -20° C. To the reaction mixture was added 100 mL of 1N HCl . The mixture was extracted once with ethyl ether. The acidic solution was made alkaline with the addition of cold 5N NaOH. The basic mixture was extracted twice with CH2Cl2. The combined organic solution was washed with a saturated NaCl solution. The CH2Cl2 solution was dried over MgSO4 and evaporated to give 4 g of an oil. Chromatography of this oil over silica gel with ethyl acetate as eluent gave 3 g (85%) of product as an oil which upon standing solidified.

後処理

  1. temperatureto warm to -20° C
  2. extractionThe mixture was extracted once with ethyl ether
  3. additionwith the addition of cold 5N NaOH
  4. extractionThe basic mixture was extracted twice with CH2Cl2
  5. washThe combined organic solution was washed with a saturated NaCl solution
  6. dry with materialThe CH2Cl2 solution was dried over MgSO4
  7. customevaporated

出典と根拠

ORDレコード
ord-09e999f577b5434db6386d46fdaa17f2
出典データセット
uspto-grants-1997_04
特許番号
US05624944

反応ノート

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