Water → HCID 10402625, compound

HRID 1110351Notes

Reaction equation

HRID 1110351 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].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[O:24].O>CCCCCC.C1(C)C=CC=CC=1>[Cl:19][C:20]1[CH:21]=[C:22]([CH:23]([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]3=[CH:9][C:8]=2[CH3:18])[OH:24])[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 10399369HCID 10399369, compoundHCID 178418339Butyllithium

Product 1

HCID 10402625HCID 10402625, compoundYield 57.2%

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 (6.0 g, 0.025 m) in toluene (30 ml). The reaction mixture was kept at -20° C. for 0.25 hours and then blown over into a cooled solution of 3-chlorobenzaldehyde (3.7 g) in toluene (30 ml) at -20° C., and allowed to warm to room temperature. Water was added and the separated organic phase extracted with 2N hydrochloric acid. This was basified with solid potassium carbonate and extracted with chloroform. The combined chloroform extracts were washed with water, dried (MgSO4) and evaporated. The solid was purified by passing through a short silica column, eluted with chloroform, then re-crystallised from diethyl ether to give the title compound (4.31 g) m.p. 123°-5° C.

Workup

  1. extractionthe separated organic phase extracted with 2N hydrochloric acid
  2. extractionextracted with chloroform
  3. washThe combined chloroform extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe solid was purified
  7. washeluted with chloroform
  8. customre-crystallised from diethyl ether

Sources & evidence

ORD record
ord-16ea105137ca4bcfb0ab5f60fad62cb4
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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