Water → Ethyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-10-Carboxylate

HRID 1458619Notes

Reaction equation

HRID 1458619 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=O.CC(C)([O-])C.[K+].O>C1COCC1>[CH:11]1[CH:12]=[CH:13][CH:14]=[C:9]2[C:10]=1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]1[CH2:5][CH2:4][CH2:3][CH2:2][N:8]12

Participants

5

Reactant 3

HCID 962WaterHCID 19599425HCID 19599425, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19599419Ethyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-10-CarboxylateYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(5-chlorovalerylamino)phenylacetate (8.10 g, 0.027 mole) in dry THF (50 ml) was added to a stirred suspension of potassium t-butoxide (7.62 g, 0.068 mole) in dry THF (200 ml) at room temperature under nitrogen. After 1 h the purple solution produced was treated with water (10 ml) and concentrated in vacuo. The residue was shaken with ethyl acetate (200 ml) and sat.ammonium chloride solution (150 ml), then the organic layer separated, dried (Na2SO4) and concentrated in vacuo to afford an orange oil. This was chromatographed on silica gel eluting with ether to afford the title compound as a yellow solid (1.25 g, 20%).

Workup

  1. customAfter 1 h the purple solution produced
  2. concentrationconcentrated in vacuo
  3. customammonium chloride solution (150 ml), then the organic layer separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford an orange oil
  7. customThis was chromatographed on silica gel eluting with ether

Sources & evidence

ORD record
ord-446d6c1042a74bb2ba3a98882d3906fb
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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