Diethyl Ether → trans-4-(2-Hydroxymethylphenyl)-1-methyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[1,2-b]pyrazine

HRID 1381072

反応式

HRID 1381072 の反応式
OCC1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@H:7]1[NH:15][CH3:16].Br[CH2:22][CH2:23]Br.C(N(CC)CC)C.[Br-].C([NH+](CC)CC)C.C([O:42][CH2:43][CH3:44])C>>[OH:42][CH2:43][C:44]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[N:5]1[CH2:23][CH2:22][N:15]([CH3:16])[C@@H:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C@@H:6]12

参加物

6

反応物 5

HCID 3283Diethyl EtherHCID 78391,2-Dibromoethane2 回HCID 8471Triethylamine2 回HCID 12493Triethylamine hydrobromideHCID 15807945trans-1-(2-Hydroxymethylanilino)-2-methylaminoindane

生成物 1

HCID 86739971trans-4-(2-Hydroxymethylphenyl)-1-methyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[1,2-b]pyrazine収率 54%

実験手順

A solution of trans 1-(2-hydroxymethylanilino)-2-methylaminoindane (1.16 kg; 4.3 moles) in 1,2-dibromoethane (7 l, 17.1 moles) and triethylamine (2.5 l; 34 moles) was added dropwise to stirred 1,2-dibromoethane (13 l; 31.9 moles) at ca. 100° over a period of 1.5 h. This was followed by triethylamine (2.5 l; 34 moles) added dropwise over 30 min. The reaction was cooled to 50° and diethyl ether (80 l) was added with good stirring. After stirring for 1 h the precipitated triethylammonium bromide was filtered off and the resulting solution concentrated in vacuo to ca 3.5 l. Addition of ethyl acetate (2.5 l) assisted crystallisation of the required product. Filtration and trituration (pet. ether) afforded the title compound as a white crystalline solid (687 g; 54%) m.p. 166-7°.

後処理

  1. additionadded dropwise over 30 min
  2. temperatureThe reaction was cooled to 50°
  3. filtrationwas filtered off
  4. concentrationthe resulting solution concentrated in vacuo to ca 3.5 l
  5. additionAddition of ethyl acetate (2.5 l)
  6. customcrystallisation of the required product
  7. filtrationFiltration and trituration (pet. ether)

出典と根拠

ORDレコード
ord-99229bb631914e70bcc59958c9111900
出典データセット
uspto-grants-1986_04
特許番号
US04585588

関連ノート

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