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

HRID 46523Notes

Reaction equation

HRID 46523 reaction equation
[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]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 128324101-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 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

Procedure

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).

Workup

  1. temperatureThe mixture is refluxed for 8 hours
  2. customevaporated
  3. extractionextracted with chloroform
  4. customThe extract is dried
  5. customevaporated
  6. customthe residue crystallized from diethyl ether

Sources & evidence

ORD record
ord-6fb0afdb6fac48e6a6600a451401beca
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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