Benzyl chloroformate → HCID 53853329, compound

HRID 1762484Notes

Reaction equation

HRID 1762484 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][CH2:22][NH2:23])#[N:11].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O1CCCC1>[C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][CH2:22][NH:23][C:25](=[O:26])[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)#[N:11]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 589265-CyanotryptamineHCID 81531Diisopropylethylamine

Product 1

HCID 53853329HCID 53853329, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisopropylethylamine (6.11 g), in dry tetrahydrofuran (20 ml) was added to a stirred solution of 5-cyano-1H-indole-3-ethanamine (7.3 g) in dry tetrahydrofuran (250 ml). A solution of benzyl chloroformate (7.73 g) in dry tetrahydroguran (20 ml) was then added at room temperature. After stirring for 1.5 h the reaction mixture was partitioned between water (100 ml). The aqueous layer was separated and extracted with ethyl acetate (4×50 ml). The combined organic solutions were washed with water (100 ml), dried (MgSO4) filtered and evaporated to afford an oily solid which was washed with petroleum spirit (b.p. 60°-80°, 100 ml) and then recrystallised from a mixture of ethyl acetate (50 ml) and petroleum spirit (b.p. 60°-80°, 35 ml) to afford the title compound (9.46 g), m.p. 127.5°-129°.

Workup

  1. customwas partitioned between water (100 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (4×50 ml)
  4. washThe combined organic solutions were washed with water (100 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an oily solid which
  9. washwas washed with petroleum spirit (b.p. 60°-80°, 100 ml)
  10. customrecrystallised from a mixture of ethyl acetate (50 ml) and petroleum spirit (b.p. 60°-80°, 35 ml)

Sources & evidence

ORD record
ord-b1ac9853ee94442f8cfd1d1c461aea38
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Reaction notes

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