Hydrogen Bromide → HCID 20343939, compound

HRID 2049644Notes

Reaction equation

HRID 2049644 reaction equation
[O:1]=[C:2]1[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.Cl[CH2:23][CH:24]1[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+].[I-].[K+].[BrH:34]>CN(C)C=O.CCOCC.O.C(Cl)(Cl)Cl>[BrH:34].[CH:24]1([CH2:23][N:15]2[CH2:14][CH2:13][C:12]3([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[O:5][C:4]4[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=4[C:2]3=[O:1])[CH2:17][CH2:16]2)[CH2:26][CH2:25]1

Participants

10

Reactant 5

HCID 260Hydrogen BromideHCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 20343882HCID 20343882, compound

Product 1

HCID 20343939HCID 20343939, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g of 10,11-dihydro-11-oxospiro-[dibenz(b,f)-oxepin-10,4'-piperidine], free base of Example 3, 0.74 g of chloromethylcyclopropane, 1.8 g of sodium bicarbonate and 1.8 g of potassium iodide in 15 ml of dimethylformamide is stirred at 70°-80° C. for 16 hours. The resulting suspension is permitted to cool before being diluted with ether and water. The organic phase is successively dried, filtered and concentrated under vacuum, leaving a viscous oil. The oil is dissolved in chloroform and the chloroform solution is passed through an alumina column, with ether as an eluant. The purified oil is dissolved in ether where it is converted to its hydrobromic acid salt which is recrystallized from a methyl alcohol-ether mixture to provide rhombic crystals, mp 258°-259° C., (dec) of 1'-cyclopropylmethyl-10,11-dihydro-11-oxospiro[dibenz(b,f)oxepin-10,4'-piperidine]hydrobromide.

Workup

  1. temperatureto cool
  2. customThe organic phase is successively dried
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customleaving a viscous oil
  6. customis recrystallized from a methyl alcohol-ether mixture

Sources & evidence

ORD record
ord-d927525e21c24bebb9adbad12692cdbe
Source dataset
uspto-grants-1980_04
Patent number
US04198418

Reaction notes

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