Hydrogen Bromide → HCID 20719741, compound

Weighed out to a reaction vessel was 250 mg (0.56 mmol) of 1,4-bis(p-toluenesulfonyl)-6-(N,N-dimethylamino)-hexahydro-1,4-diazepine synthesized by the above process, and 0.20 ml (2.3 mmol) of phenol and a 30% acetic acid solution (4 ml) of hydrobromic acid were added, followed by stirring for 6 hours in a bath controlled to 70° C. After the reaction mixture was concentrated under reduced pressure, diethyl ether (5 ml) was added to the residue with stirring, and a supernatant was removed. This process was repeated twice to remove diethyl ether-soluble material. The residue was concentrated again under reduced pressure to completely remove diethyl ether. Ethanol (2 ml) was added to the resultant residue, and the mixture was stirred for 30 minutes. Diethyl ether (2 ml) was added to the resultant solution, and the mixture was cooled in an ice bath, thereby obtaining 194 mg (yield: 91%) of the title compound as a colorless crystalline powder (melting point: 245° C., decomposed).

1. customWeighed out to a reaction vessel was
2. customcontrolled to 70° C
3. concentrationAfter the reaction mixture was concentrated under reduced pressure, diethyl ether (5 ml)
4. additionwas added to the residue
5. stirringwith stirring
6. customa supernatant was removed
7. customto remove diethyl ether-soluble material
8. concentrationThe residue was concentrated again under reduced pressure to completely remove diethyl ether
9. additionEthanol (2 ml) was added to the resultant residue
10. stirringthe mixture was stirred for 30 minutes
11. additionDiethyl ether (2 ml) was added to the resultant solution
12. temperaturethe mixture was cooled in an ice bath

ORD record

ord-7e25013841084a689e20b5086688571c

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828316B2