Water → HCID 22381731, compound

HRID 895775Notes

Reaction equation

HRID 895775 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([NH:7][CH2:8][C:9]1[C:17]2[NH:16][C:15]3[CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:6].O>CN(C=O)C>[CH2:4]1[N:16]2[C:17]3[C:13]([C:14]4[CH2:20][CH2:19][CH2:18][C:15]=42)=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:8][NH:7][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 22381724HCID 22381724, compound

Product 1

HCID 22381731HCID 22381731, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (124 mg, 3.10 mmol) in DMF (3 mL), 2-chloro-N-(1,2,3,4-tetrahydrocyclopenta[b]indol-5-ylmethyl)acetamide (135 mg, 0.515 mmol) in DMF (3 mL) was added at rt under Ar. After 16 h, H2O (2 mL) was added to quench the excess reagent, H2 evolved upon addition. After an additional 30 min, CHCl3 (20 mL) and H2O (10 mL) were added. The two layers were separated. The aqueous layer was extracted with CHCl3 (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification on SiO2, eluted with (30:1) CHCl3:CH3OH gave 67 mg (58%) of the title compound as a brown solid.

Workup

  1. additionwas added at rt under Ar
  2. customto quench the excess reagent, H2
  3. additionevolved upon addition
  4. waitAfter an additional 30 min
  5. additionCHCl3 (20 mL) and H2O (10 mL) were added
  6. customThe two layers were separated
  7. extractionThe aqueous layer was extracted with CHCl3 (10 mL)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification on SiO2
  12. washeluted with (30:1) CHCl3

Sources & evidence

ORD record
ord-73f05b65b1dc4cc28fe9f2f0fbe1d678
Source dataset
uspto-grants-2005_07
Patent number
US06916922B2

Reaction notes

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