Water → HCID 57966530, compound

HRID 420566Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][O:17][C:18]4[CH:19]=[C:20]([CH2:25][C:26]#N)[CH:21]=[CH:22][C:23]=4[CH3:24])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[OH-:30].[Na+].[OH2:32]>C(O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][O:17][C:18]4[CH:19]=[C:20]([CH2:25][C:26]([OH:32])=[O:30])[CH:21]=[CH:22][C:23]=4[CH3:24])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of [3-{2-[1-(6-chlorobenzothiazole-2-yl)piperidine-4-yl]ethoxy}-4-methylphenyl]acetonitrile (1.14 g; 2.68 mmol), sodium hydroxide (0.54 g; 13.5 mmol), water (1.6 ml) and ethanol (21 ml) was stirred at 80° C. for 6 hours. The reaction solution was concentrated under reduced pressure and became pH=7 with 2N-aqueous hydrochloric acid. The precipitate was collected to give 3-{2-[1-(6-chlorobenzothiazole-2-yl)piperidine-4-yl]ethoxy}-4-methylphenyl acetic acid as colorless crystal (0.63 g; 53%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customThe precipitate was collected

Sources & evidence

ORD record: ord-d7d75c105735443586eee7267668d07f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097610B2

Reaction notes

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