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

HRID 491456Notes

Reaction equation

HRID 491456 reaction equation
C[C@H](N)C1C=CC=CC=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:15]([C@H:17]1[CH2:25][CH:24]=[CH:23][CH2:22][C@H:18]1[C:19]([OH:21])=O)=O.[ClH:31].Cl.[NH:33]1[CH2:38][CH2:37][CH:36]([NH:39][NH2:40])[CH2:35][CH2:34]1.C(N(CC)CC)C>C(O)CC>[ClH:31].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:15]2[C@@H:17]3[C@@H:18]([CH2:22][CH:23]=[CH:24][CH2:25]3)[C:19](=[O:21])[N:39]([CH:36]3[CH2:37][CH2:38][NH:33][CH2:34][CH2:35]3)[N:40]=2)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 758181-Phenethylamine, (-)-HCID 11087524cis-2-(3,4-Dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid2×HCID 223113172,6-Dichloro-3-fluoroacetophenone

Product 1

HCID 68878851(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

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.

Workup

  1. filtrationthe precipitate is filtered off
  2. customdried

Sources & evidence

ORD record
ord-3e7ab68a8eb54c8c9af990e155f5c890
Source dataset
uspto-grants-2009_05
Patent number
US07531540B2

Reaction notes

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