Oxalic Acid → HCID 71295426, compound

HRID 1774702Notes

Reaction equation

HRID 1774702 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:30]=[C:29]5[C:24]([CH:25]=[CH:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>ClCCl.CO>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:30]=[C:29]5[C:24]([CH:25]=[CH:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:14][CH2:15]3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 11978813Brexpiprazole

Product 1

HCID 71295426HCID 71295426, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-butoxy]-1H-quinolin-2-one (3 g) in dichloromethane (20 ml) and methanol (20 ml) was warmed to 60° C., dissolved, and oxalic acid (0.69 g) dissolved in methanol (5 ml) was added at room temperature. The precipitated crystals were collected by filtration, and dried to give 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-butoxy]-1H-quinolin-2-one oxalate (3.3 g).

Workup

  1. dissolutiondissolved
  2. additionwas added at room temperature
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-921c2d5046d9487b86b8012e9ec135b8
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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