Formic Acid → 1-[2-(N-isopropyl-N-methylamino)propyl]-3-hydroxymethyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

반응식

[CH2:1]=O.[CH:3]([NH:6][CH:7]([CH3:27])[CH2:8][C:9]1[C:10](=[O:26])[NH:11][CH2:12][CH2:13][CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[C:15]=12)([CH3:5])[CH3:4].[CH:28]([OH:30])=O>>[CH:3]([N:6]([CH:7]([CH3:27])[CH2:8][C:9]1[C:10](=[O:26])[N:11]([CH2:28][OH:30])[CH2:12][CH2:13][CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[C:15]=12)[CH3:1])([CH3:4])[CH3:5]

참가 물질

반응물 3

HCID 284Formic Acid

HCID 712Formaldehyde

HCID 128324101-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

생성물 1

HCID 128324721-[2-(N-isopropyl-N-methylamino)propyl]-3-hydroxymethyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

실험 절차

24.4 ml of 37 percent aqueous formaldehyde are added to the stirred suspension of 10.3 g of slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one (Example 1) in 15.7 ml of formic acid. The mixture is refluxed for 8 hours, evaporated and the residue suspended in water. The mixture is basified to pH=10-11 with 3 N aqueous sodium hydroxide and extracted with chloroform. The extract is dried, evaporated, and the residue crystallized from diethyl ether, to give the 1-[2-(N-isopropyl-N-methylamino)-propyl]-3-hydroxymethyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one melting at 158°-161°, (R,R-isomer).