Hydrochloric Acid → alpha,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

HRID 2287129ノート

反応式

HRID 2287129 の反応式
CN.Cl.[C:4]1([C:10]2([CH2:16][C:17](=O)[CH3:18])[CH:15]=[CH:14][CH2:13][CH:12]=[CH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20]([BH3-])#[N:21].[Na+]>CCOCC.CO>[CH3:18][CH:17]([NH:21][CH3:20])[CH2:16][C:10]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:15]=[CH:14][CH2:13][CH:12]=[CH:11]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 23459472(1-Phenyl-2,5-cyclohexadien-1-yl)-2-propanone

生成物 1

HCID 23459460alpha,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

To 11.5 ml. (about 6 equivalents) of methylamine and 10 g. of molecular sieve 3A in 200 ml. of absolute methanol are added dropwise at 0° C. 17.8 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and subsequently 9.4 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of methanol. After the addition of 1.95 g. (0.75 equivalent) of sodium cyanoborohydride, the mixture is stirred at room temperature for 5 days. The mixture is worked-up as follows: The mixture is treated with ice-water and ether and extracted with 3 N aqueous hydrochloric acid. The hydrochloric acid extracts are made basic with concentrated aqueous ammonia and extracted with ether. The ether phase is dried with sodium sulfate, filtered and evaporated. The crude product obtained is chromatographed on silica gel with methylene chloride/methanol (10:1). There is obtained α,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine in the form of an oily product. This is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 155°-158° C.

後処理

  1. additionAfter the addition of 1.95 g
  2. extractionextracted with 3 N aqueous hydrochloric acid
  3. extractionextracted with ether
  4. dry with materialThe ether phase is dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product obtained
  8. customis chromatographed on silica gel with methylene chloride/methanol (10:1)

出典と根拠

ORDレコード
ord-0d3d3d63863048dd8ea2246cf59c45ab
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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