Benzoyl chloride → HCID 67988194, compound

HRID 2168208Notes

Reaction equation

HRID 2168208 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[CH2:15][O:16][CH3:17].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl>[CH3:17][O:16][CH2:15][CH:3]1[CH:2]([NH:1][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:25])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67974439HCID 67974439, compound

Product 1

HCID 67988194HCID 67988194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl 4-amino-3-[(methyloxy)methyl]-1-piperidinecarboxylate D33 (0.7 g), and benzoyl chloride (490 mg, 3.5 mmol, commercially available from e.g. Sigma-Aldrich, Fluka or Fisher) were dissolved in dichloromethane (30 ml) and then triethylamine (1.3 ml, 8.7 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours, then washed with water (2×), brine, dried with MgSO4, filtered and solvent removed to obtain a yellow oil of crude product which was purified by column chromatography on silica gel eluting with pet eth/EA (2/1) to give clean desired product D34 as a yellow oil in 0.8 g. LCMS [M-56+H] [email protected] min (5 min run)

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customsolvent removed
  5. customto obtain a yellow oil of crude product which
  6. customwas purified by column chromatography on silica gel eluting with pet

Sources & evidence

ORD record
ord-bcf64d64d9e144b6bf9ca10d6bdc498c
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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