1-Phenethylamine, (-)- → (4aS,8aR)-4-(3,4-Diethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one hydrochloride

HRID 585484Notes

Reaction equation

HRID 585484 reaction equation
C[C@H](N)C1C=CC=CC=1.[CH2:10]([O:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH3:32])[C:16]([C@H:18]1[CH2:26][CH:25]=[CH:24][CH2:23][C@H:19]1[C:20]([OH:22])=O)=O)[CH3:11].[ClH:33].Cl.[NH:35]1[CH2:40][CH2:39][CH:38]([NH:41][NH2:42])[CH2:37][CH2:36]1>CC(O)C>[ClH:33].[CH2:10]([O:12][C:13]1[CH:14]=[C:15]([C:16]2[C@@H:18]3[C@@H:19]([CH2:23][CH:24]=[CH:25][CH2:26]3)[C:20](=[O:22])[N:41]([CH:38]3[CH2:39][CH2:40][NH:35][CH2:36][CH2:37]3)[N:42]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH3:32])[CH3:11]

Participants

5

Reactant 3

HCID 758181-Phenethylamine, (-)-HCID 10925192(cis)-2-(3,4-Diethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid2×HCID 223113172,6-Dichloro-3-fluoroacetophenone

Product 1

HCID 68877453(4aS,8aR)-4-(3,4-Diethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Prepared from the salt of (S)-(−)-α-methylbenzylamine, (cis)-2-(3,4-diethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid (compound P) and piperidin-4-yl-hydrazine dihydrochloride in 2-propanol as described for compound 5d. M. p. 248-250° C.

Sources & evidence

ORD record
ord-9955cfde85604f27bcee8f419b85b889
Source dataset
uspto-grants-2005_08
Patent number
US06933296B2

Reaction notes

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