2-chloro-N-cyclopropylmethyl-N-[2-(3-phenyl1H-indol-2-yl)ethyl]acetamide → 2,3-dihydro-3-cyclopropylmethyl-11-phenyl-1H-[1,4]diazepino[1,7-a]indol-4(5H)-one

HRID 652720

Reaktionsgleichung

Reaktionsgleichung von HRID 652720
Cl[CH2:2][C:3]([N:5]([CH2:23][CH:24]1[CH2:26][CH2:25]1)[CH2:6][CH2:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:4]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.[OH-].[Na+].O>[CH:24]1([CH2:23][N:5]2[CH2:6][CH2:7][C:8]3=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]3[CH2:2][C:3]2=[O:4])[CH2:26][CH2:25]1

Komponenten

6

Edukt 1

HCID 142103702-chloro-N-cyclopropylmethyl-N-[2-(3-phenyl1H-indol-2-yl)ethyl]acetamide

Produkt 1

HCID 142103712,3-dihydro-3-cyclopropylmethyl-11-phenyl-1H-[1,4]diazepino[1,7-a]indol-4(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 184.3 g 2-chloro-N-cyclopropylmethyl-N-[2-(3-phenyl-1H-indol-2-yl)ethyl]acetamide in 1843 ml methylene chloride is added dropwise under vigorous stirring to a suspension of 17.9 g N-benzyltributyl-ammoniumbromide in 1843 ml methylene chloride and 921 ml 30% sodium hydroxide. The mixture is stirred for further 10 minutes and diluted with 1 l water. The organic phase is separated, washed with water, dried and evaporated to dryness. The residue is dissolved in 500 ml boiling ethanol, cooled and treated with 500 ml ether. The resulting cristalline precipitate is filtered off, washed with ethanol/ather (1:1) and then ether to give 2,3-dihydro-3-cyclopropylmethyl-11-phenyl-1H-[1,4]diazepino[1,7-a]indol-4(5H)-one, m.p. 149°-150°.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with water
  3. customdried
  4. customevaporated to dryness
  5. dissolutionThe residue is dissolved in 500 ml
  6. temperaturecooled
  7. additiontreated with 500 ml ether
  8. filtrationThe resulting cristalline precipitate is filtered off
  9. washwashed with ethanol/ather (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-269af1cc43ba49e99273bb649c792914
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04673674

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