2,4-Dichlorobenzaldehyde → 4-Chloro-2-[4-(2,4-dichloro-benzyl)-piperazin-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927498Notes

Reaction equation

HRID 1927498 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:29])[C:8]2[O:14][C:13]3[C:15]([Cl:25])=[CH:16][C:17]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:18][C:12]=3[CH2:11][S:10](=[O:27])(=[O:26])[C:9]=2[CH:28]=1)=[O:4].[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH:33]=O.C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:29])[C:8]2[O:14][C:13]3[C:15]([Cl:25])=[CH:16][C:17]([N:19]4[CH2:20][CH2:21][N:22]([CH2:33][C:32]5[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:31]=5[Cl:30])[CH2:23][CH2:24]4)=[CH:18][C:12]=3[CH2:11][S:10](=[O:26])(=[O:27])[C:9]=2[CH:28]=1)=[O:4]

Participants

6

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284804-Chloro-2-[4-(2,4-dichloro-benzyl)-piperazin-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

Titanium isopropoxide (0.25 mL, 0.82 mmol) was added to solution of Example 104k (0.3 g, 0.68 mmol) and 2,4-dichlorobenzaldehyde (0.120 g, 0.68 mmol) in dry methanol (10 mL). The reaction mixture was processed as described in the synthesis of Example 108k using sodium cyanoborohydride (0.041 g, 0.65 mmol) to obtain the title compound as a white solid. Yield: 0.285 g, (68.69%); 1H NMR (DMSO-d6): δ 2.60-2.80 (m, 7H, 2CH2, CH3), 3.20-3.35 (m, 4H, 2CH2), 3.95 (s, 3H, OCH3), 4.65 (s, 2H, CH2), 6.80 (d, 1H, Ar), 6.90 (d, 1H, Ar), 7.25-7.45 (m, 3H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (ES+) 596 (M+1).

Workup

  1. customas described in the synthesis of Example 108k

Sources & evidence

ORD record
ord-61aefe4986464f909816101cfc06955e
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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