Ethylene Oxide → HCID 20387293, compound

HRID 46528Notes

Reaction equation

HRID 46528 reaction equation
[CH:1]([NH:4][CH:5]([CH3:25])[CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12)([CH3:3])[CH3:2].[CH2:26]1[O:28][CH2:27]1>C(O)C>[CH:1]([N:4]([CH:5]([CH3:25])[CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12)[CH2:26][CH2:27][OH:28])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6354Ethylene Oxide2×HCID 128324101-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 1

HCID 20387293HCID 20387293, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 5 g of slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one and 14.75 ml of liquified ethylene oxide in 100 ml of absolute ethanol is stirred in a sealed pressure tube at room temperature for two days. The reaction mixture is recharged with an additional 14.75 ml portion of ethylene oxide and stirred for four additional days at room temperature. It is evaporated, the residue slurried in diethyl ether, collected by filtration and recrystallized from ethyl acetate to yield the 1-[2-(N-isopropyl-N-2-hydroxyethylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, RR racemate melting at 147°-149°.

Workup

  1. additionThe mixture of 5 g
  2. stirringstirred for four additional days at room temperature
  3. customIt is evaporated
  4. filtrationcollected by filtration
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e2039377bfee433b9b961f74de835854
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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