Borane,N-dimethylmethanamine (1:1) → 2-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

HRID 988630Notes

Reaction equation

HRID 988630 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[N:15][C:16]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[B-][N+](C)(C)C>C(O)(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 219061692-(1-Boc-piperidin-4-ylmethylidene)amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

Product 1

HCID 219066432-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamideYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution containing 2-(1-Boc-piperidin-4-yl-methylidene)amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide from above (6.0 g, 13 mmol) and borane trimethylamine complex (2.9 g, 39 mmol) in glacial acetic acid (100 mL) was heated at 70°0 C. for 24 h. The solution was allowed to cool to room temperature; then the solvent was removed in vacuo, and the residue was partitioned between dichloromethane (200 mL) and water (100 mL). The biphasic mixture was treated with 2 N NaOH until neutral; then the organic layer was separated and the aqueous layer was washed again with dichloromethane (100 mL). The combined organic layers were washed with brine (100 mL), dried with MgSO4, and filtered. The filtrate was concentrated in vacuo to give 5.85 g (97%) of the title compound as an orange foam which was used directly in the next step without further purification.

Workup

  1. temperaturewas heated at 70°0 C
  2. customthen the solvent was removed in vacuo
  3. customthe residue was partitioned between dichloromethane (200 mL) and water (100 mL)
  4. additionThe biphasic mixture was treated with 2 N NaOH until neutral
  5. customthen the organic layer was separated
  6. washthe aqueous layer was washed again with dichloromethane (100 mL)
  7. washThe combined organic layers were washed with brine (100 mL)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-92a443ceabab4fc1b48e3fa032319462
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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