Hydrochloric Acid → (5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-3-yl)methanol

HRID 972637Notes

Reaction equation

HRID 972637 reaction equation
C([Li])CCC.[CH:6]1[N:7]=[CH:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=12.[CH2:15]=[O:16].Cl>CCCCCC.CCOCC>[OH:16][CH2:15][C:8]1[N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 141931035H,6H,7H,8H-imidazo(1,5-a)pyridineHCID 178418339Butyllithium

Product 1

HCID 12923422(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.58 molar n-butyl lithium in n-hexane (49 ml.) was added over 0.5 hour to a stirred solution of 5,6,7,8-tetrahydroimidazo[1,5-a]pyridine (8.9 g.) in dry ether at -60° under nitrogen. After 3 hours, gaseous formaldehyde generated by the thermal condensation of paraformaldehyde (6.9 g.) was passed into the red solution. The mixture was allowed to warm to room temperature overnight, acidified with hydrochloric acid and extracted with chloroform. The aqueous layer was basified with an excess of saturated sodium carbonate solution and extracted with chloroform. Concentration and recrystallisation of the residue from ethanol-ethyl acetate-petroleum ether afforded 3-hydroxymethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine (7.7 g.), m.p. 188°-199°.

Workup

  1. extractionextracted with chloroform
  2. extractionextracted with chloroform
  3. concentrationConcentration and recrystallisation of the residue from ethanol-ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-e739e17be9d74790a7cb1f8f6662e3f8
Source dataset
uspto-grants-1977_10
Patent number
US04053473

Reaction notes

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