Water → HCID 10333259, compound

HRID 1494541Notes

Reaction equation

HRID 1494541 reaction equation
C([Li])CCC.Br[C:7]1[N:12]=[C:11]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]2=[CH:9][C:8]=1[CH3:18].[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=1.O>CCCCCC.C1(C)C=CC=CC=1>[CH3:18][C:8]1[CH:9]=[C:10]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]2=[N:12][C:7]=1[CH:25]([C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[OH:26]

Participants

7

Reactant 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 10399369HCID 10399369, compoundHCID 178418339Butyllithium

Product 1

HCID 10333259HCID 10333259, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of 1.6M n-butyl lithium in n-hexane (16.5 ml) in toluene (20 ml) at -20° C., under nitrogen, was added a solution of 2-bromo-6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyridine (6 g, 0.025 m) in toluene (30 ml) and kept at -20° C. for 0.25 hours. This was blown over into a solution of 3-pyridine carboxaldehyde (2.7 g) in toluene (30 ml) kept at -20° C. The solution was allowed to warm up to room temperature and water added. The organic phase was separated, dried (MgSO4) and evaporated. The solid was recrystallised from ether (twice) to give 1-(6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyrid-2-yl)-1-(pyrid-3-yl)methanol (4.32 g, 64%) m.p. 124°-6° C.

Workup

  1. customkept at -20° C
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe solid was recrystallised from ether (twice)

Sources & evidence

ORD record
ord-0c904d2bf015442a872a46ff4e2fe6b7
Source dataset
uspto-grants-1991_06
Patent number
US05026854

Reaction notes

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