Phosgene → HCID 13534259, compound

HRID 464420Notes

Reaction equation

HRID 464420 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([N:12]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][CH2:22]3)[CH2:13]1)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:22]1[C:23]2[C:19](=[C:18]([O:17][CH:14]3[CH2:15][CH2:16][N:12]([C:1]([Cl:4])=[O:2])[CH2:13]3)[CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20262989HCID 20262989, compound

Product 1

HCID 13534259HCID 13534259, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 6.9 g (0.07 mole) of phosgene in 100 ml of anhydrous benzene under nitrogen gas and cooled at 10° C. was added dropwise a solution of 18.13 g (0.062 mole) of 1-benzyl-3-(4-indanyloxy)pyrrolidine in 50 ml of dry benzene. After stirring for 18 hr, the slightly turbid reaction mixture was filtered through celite. The filtrate was washed with 50 ml of ice-water, dried over magnesium sulfate and concentrated on a rotary evaporator. The solid residue was triturated with boiling isopropyl ether. Fifteen grams of crude product was obtained by filtering the mixture. Recrystallization from a mixture of benzene and 30/60 petroleum ether gave 13.1 g of cream colored solid, m.p. 128°-129° C.

Workup

  1. customthe slightly turbid reaction mixture
  2. filtrationwas filtered through celite
  3. washThe filtrate was washed with 50 ml of ice-water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe solid residue was triturated with boiling isopropyl ether

Sources & evidence

ORD record
ord-989ca656e4b8485b86a697ab013e7a4e
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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