HCID 70456153, compound → HCID 12946401, compound

HRID 1380630Notes

Reaction equation

HRID 1380630 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH:15]([Br:16])[CH2:14][CH2:13][C:12]3[N:11]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:10]=[CH:9][C:8]2=3)[O:4]1>C(N)(C)C>[CH:12]([NH:11][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH:15]([Br:16])[CH2:14][CH2:13][C:12]3[N:11]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:10]=[CH:9][C:8]2=3)[O:4]1)([CH3:13])[CH3:8]

Participants

3

Reactant 1

HCID 70456153HCID 70456153, compound

Product 1

HCID 12946401HCID 12946401, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6363IsopropylamineSolvent

Procedure

A solution of 4'-chloromethyl-5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-[1,3]dioxolane (100 parts) in isopropylamine (890 parts) is placed in a sealed tube and heated on boiling water bath for 7 hours. The reaction mixture is evaporated to remove isopropylamine. The residue is dissolved in dichloromethane, washed with water, dried and concentrated to afford 4'-isopropylaminomethyl-5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-[1,3]dioxolane in 60% yield. The physical constants are given in Table I, No. 19.

Workup

  1. temperatureheated
  2. customfor 7 hours
  3. customThe reaction mixture is evaporated
  4. customto remove isopropylamine
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-17a1919881f745eb934bc564eb3364d9
Source dataset
uspto-grants-1986_04
Patent number
US04582905

Reaction notes

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