Pyridine → HCID 131723706, compound

HRID 2298113Notes

Reaction equation

HRID 2298113 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[I-].[Li+].Br[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:31])=[C:15]([CH:30]=1)[C:16]([NH:18][CH2:19][C:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2)=[O:17].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[ClH:31].[Cl:31][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH:36]2[CH:35]=[CH:34][CH2:33][NH:32][CH2:37]2)=[CH:30][C:15]=1[C:16]([NH:18][CH2:19][C:20]12[CH2:21][CH:22]3[CH2:23][CH:24]([CH2:25][CH:26]([CH2:28]3)[CH2:27]1)[CH2:29]2)=[O:17]

Participants

5

Reactant 4

HCID 1049Pyridine3×HCID 66321Lithium iodideHCID 21226445Aluminium lithium hydrideHCID 219000205-Bromomethyl-2chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 131723706HCID 131723706, compound

Procedure

To pyridine (6 ml) at 0° C. was added portionwise lithium aluminium hydride (0.24 g). The mixture was allowed to warm to room temperature and was stirred for 24 h. Lithium iodide (0.220 g) and pyridine (1 ml) were added and the reaction stirred for a further 1 h. 5-Bromomethyl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g, Example 8b) in dry pyridine (2 ml) was added to the solution at room temperature. After 2 h, the mixture was quenched at 0° C. with a cold 15% aqueous solution of acetic acid, stirred for an hour and concentrated under vacuum. The residue was taken in 1N sodium hydroxide, extracted with dichloromethane and the organic layers dried over magnesium sulfate. The crude material was purified on silicagel (2 to 10% 7N ammonia in methanol/dichloromethane) then treated with a 4N solution of hydrogen chloride in dioxane and methanol to give the title compound (0.20 g).

Workup

  1. stirringthe reaction stirred for a further 1 h
  2. waitAfter 2 h
  3. customthe mixture was quenched at 0° C. with a cold 15% aqueous solution of acetic acid
  4. stirringstirred for an hour
  5. concentrationconcentrated under vacuum
  6. extractionextracted with dichloromethane
  7. dry with materialthe organic layers dried over magnesium sulfate
  8. customThe crude material was purified on silicagel (2 to 10% 7N ammonia in methanol/dichloromethane)
  9. additionthen treated with a 4N solution of hydrogen chloride in dioxane and methanol

Sources & evidence

ORD record
ord-c7eb6277971044ca90bfb68fed2c426b
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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