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

HRID 980510

反応式

HRID 980510 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 drop-wise 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 drop-wise 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-0c5a66fa6bf74a91af67dd31580719ff
出典データセット
uspto-grants-1987_01
特許番号
US04638066

関連ノート

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