Water → HCID 22381724, compound

HRID 895774Notes

Reaction equation

HRID 895774 reaction equation
[CH2:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([CH2:13][NH2:14])[C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:21][CH2:22][C:23](Cl)=[O:24].O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:21][CH2:22][C:23]([NH:14][CH2:13][C:7]1[C:6]2[NH:5][C:4]3[CH2:3][CH2:2][CH2:1][C:12]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 22381732HCID 22381732, compound

Product 1

HCID 22381724HCID 22381724, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydrocyclopenta[b]indol-5-ylmethylamine (100 mg, 0.538 mmol) and pyridine (0.1 mL, 1.23 mmol) in CH2Cl2 (2 mL) was cooled to 0-5° C. in an ice-bath under Ar before chloroacetyl chloride (62 μL, 0.59 mmol) was added. After 1 h, the ice-bath was removed to allow the reaction to warm to rt. After an additional 12 h, H2O (3 mL) and CHCl3 (3 mL) were added. The two layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification on SiO2, eluted with (40:1) CHCl3:CH3OH gave 80 mg (57%) of the title compound as a yellow solid.

Workup

  1. additionwas added
  2. customthe ice-bath was removed
  3. customthe reaction
  4. waitAfter an additional 12 h
  5. customThe two layers were separated
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification on SiO2
  10. washeluted with (40:1) CHCl3

Sources & evidence

ORD record
ord-78b0581c689e4cc9b76722f0e2e2f17a
Source dataset
uspto-grants-2005_07
Patent number
US06916922B2

Reaction notes

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