Reaktion #578638

ord-3e7ab68a8eb54c8c9af990e155f5c890

Reaktionsgleichung

C[C@H](N)c1ccccc1
(S)-(−)-α-methylbenzylamine
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
(cis)-2-(3,4-dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
compound A8
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
(cis)-2-(3,4-dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid
Cl.Cl.NNC1CCNCC1
piperidin-4-yl-hydrazine dihydrochloride
CCN(CC)CC
triethylamine
→
COc1ccc(C2=NN(C3CCNCC3)C(=O)[C@@H]3CC=CC[C@H]23)cc1OC.Cl
(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one hydrochloride

Edukte

—
salt
C[C@H](N)c1ccccc1
(S)-(−)-α-methylbenzylamine
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
(cis)-2-(3,4-dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
compound A8
COc1ccc(C(=O)[C@H]2CC=CC[C@H]2C(=O)O)cc1OC
(cis)-2-(3,4-dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid
Cl.Cl.NNC1CCNCC1
piperidin-4-yl-hydrazine dihydrochloride
CCN(CC)CC
triethylamine

Reagenzien

Keine

Lösungsmittel

CCCO
1-propanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe precipitate is filtered off
  2. 2
    Sonstigedried

Vorschrift

A solution of 50 mmol of the salt of (S)-(−)-α-methylbenzylamine and (cis)-2-(3,4-dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid (starting compound A8), 55 mmol of piperidin-4-yl-hydrazine dihydrochloride and 100 mmol of triethylamine in 150 ml of 1-propanol is refluxed for 18 h. After cooling to RT, the precipitate is filtered off and dried. M.p. 285-288° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07531540B2uspto-grants-2009_05