Ammonia → 4-(Imidazo[1,2-a]pyridin-3-yl)piperidin-4-ol

HRID 1768032Notes

Reaction equation

HRID 1768032 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([OH:23])([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.N>C(Cl)Cl>[N:16]1[CH:15]=[C:14]([C:11]2([OH:23])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[N:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=12

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69456650HCID 69456650, compound

Product 1

HCID 236144534-(Imidazo[1,2-a]pyridin-3-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-hydroxy-4-imidazo[1,2-a]pyridin-3-yl-piperidine-1-carboxylic acid tert-butyl ester (2.0 g 6.26 mmol) in CH2Cl2 (100 ml) trifluoro acetic acid (10 ml) was added at room temperature. The reaction mixture was stirred at room temperature for 24 hrs. At the end, the reaction mixture was basified with methanolic ammonia and concentrated to dryness. The residue was directly chromatographed over silica-gel column and eluted with methanol:10% methanolic ammonia. The product, 4-imidazo[1,2-a]pyridin-3-yl-piperidin-4-ol was obtained as yellow oil; Yield; 620 mg (48%); 218 (M+H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was directly chromatographed over silica-gel column
  3. washeluted with methanol

Sources & evidence

ORD record
ord-3a5b1d94642e402d8a067c1d4b7dd0fe
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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