Formaldehyde → HCID 19367098, compound

HRID 1416291Notes

Reaction equation

HRID 1416291 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.C=O.C1C[O:31][CH2:30]C1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:30][OH:31])=[C:9]([CH2:11][N:12]3[CH2:13][CH2:14][N:15]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[CH2:16][CH2:17]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 712Formaldehyde3×HCID 8028TetrahydrofuranHCID 19367120HCID 19367120, compound

Product 1

HCID 19367098HCID 19367098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 6-chloro-2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridine (Example 31, Step 2; 0.125 g), 37% formaldehyde in water (2 mL), and THF (2 mL) is stirred at 85° C. for 50 min, at which time an additional 1 mL of 37% formaldehyde in water is added. A third addition of 37% formaldehyde in water (1 mL) is made 1.5 h later. After the mixture has stirred for a total of 22 h, the heat is turned off and the mixture is allowed to stir at room temperature an additional 12 h. The mixture is then partitioned between dichloromethane and aq. sodium bicarbonate. Chromatography on silica gel using methanol/dichloromethane (3/97) gives 0.132 g of product, which after crystallization from dichloromethane/hexane gives 0.125 g of the title compound; mp 165-166° C.; MS m/z 424, 426; IR (mineral oil) 1479, 792, 1021, 816, 1502 cm-1. 1H NMR (CDCl3) δ2.79, 3.05, 3.90, 4.93, 6.1, 6.92, 7.17, 7.35, 7.52, 8.04.

Workup

  1. additionis added
  2. stirringto stir at room temperature an additional 12 h
  3. customThe mixture is then partitioned between dichloromethane and aq. sodium bicarbonate

Sources & evidence

ORD record
ord-9951aeddb060463fae83807b972dbc6f
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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