Sodium Hydroxide → 7-Hydroxy-n-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-4-phenylphthalazin-1-amine

HRID 30044

Reaction equation

HRID 30044 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:8][N:9]=[C:10]2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[Na+]>>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[N:8][N:9]=[C:10]2[NH:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)[CH2:18][CH2:19]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 115546837-methoxy-N-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-4-phenylphthalazin-1-amine2×HCID 21584435Pyridinium hydrochloride

Product 1

HCID 1363949037-Hydroxy-n-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-4-phenylphthalazin-1-amineYield 86.8%

Conditions

Temperature
210 °C

Procedure

A mixture of 597 mg (1.25 mmol) of 7-methoxy-N-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-4-phenylphthalazin-1-amine (compound 1) and pyridinium hydrochloride is heated at 210° C. for 45 minutes. The reaction medium is cooled and 1N sodium hydroxide solution is then added. A precipitate forms, which is washed with water and with dichloromethane, and then dried under reduced pressure. 500 mg of a beige-coloured powder are obtained.

Workup

  1. temperatureThe reaction medium is cooled
  2. washA precipitate forms, which is washed with water and with dichloromethane
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e9b7e2235a7a47bfab84ebdfc02c564b
Source dataset
uspto-grants-2008_09
Patent number
US07423030B2

Linked notes

Loading…