Hydrochloric Acid → alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine hydrochloride

HRID 2287134ノート

反応式

HRID 2287134 の反応式
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[ClH:6].[C:7]1([C:13]2([CH2:19][C:20](=O)[CH3:21])[CH:18]=[CH:17][CH2:16][CH:15]=[CH:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#N.[Na+]>CO>[ClH:6].[CH3:21][CH:20]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:19][C:13]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:18]=[CH:17][CH2:16][CH:15]=[CH:14]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 5003444Sodium cyanoborohydrideHCID 23459472(1-Phenyl-2,5-cyclohexadien-1-yl)-2-propanone

生成物 1

HCID 23459443alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To 27.5 ml. (about 6 equivalents) of diethylamine and 10 g. of molecular sieve 3A in 200 ml. of methanol are added at 0° C. 17.6 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and then 9.4 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of methanol and finally 1.95 g. (0.7 equivalents) of sodium cyanoborohydride. The mixture is stirred at room temperature for 5 days and then worked-up in exactly the same manner as described in Example 16. There is obtained an oily residue which is chromatographed on a silica gel thick-layer plate with ethyl acetate/triethylamine (15:1). Two products are scratched off and eluted with methylene chloride/methanol (4:1). The product of RF 0.32 is α-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine. The other product (RF 0.54) is the desired product, namely, α-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine. This is converted as usual into the hydrochloride and recrystallized from methylene chloride/ether. According to melting point and mixed melting point, the product is identical with that obtained in accordance with Example 18.

後処理

  1. customThere is obtained an oily residue which
  2. customis chromatographed on a silica gel thick-layer plate with ethyl acetate/triethylamine (15:1)
  3. washeluted with methylene chloride/methanol (4:1)
  4. customrecrystallized from methylene chloride/ether
  5. additionmixed
  6. customthat obtained in accordance with Example 18

出典と根拠

ORDレコード
ord-026ead067bc74d2f84a5ace4bba0b2d9
出典データセット
uspto-grants-1981_05
特許番号
US04269788

反応ノート

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