Ammonia → HCID 66939016, compound

HRID 1716916Notes

Reaction equation

HRID 1716916 reaction equation
C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=2)[CH2:16][CH2:15]1.[C:28]([Cl:34])(=[O:33])[CH2:29][CH:30]([CH3:32])[CH3:31].N.[NH4+].[Cl-]>CO.C(Cl)Cl>[ClH:34].[CH3:31][CH:30]([CH3:32])[CH2:29][C:28]([NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([NH:20][CH:17]2[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]2)[CH:22]=1)=[O:33]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 66054Isovaleryl chlorideHCID 66939057HCID 66939057, compound

Product 1

HCID 66939016HCID 66939016, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Combine 1-methyl-4-(3-aminophenylamino)piperidine triacetate (Preparation 18, 460 mg, 1.17 mmol) and CH2Cl2 (13 mL); stir and cool to 0° C. Add isovaleryl chloride (135 μL, 1.05 mmol), and stir at room temperature for 18 hr. Load onto a 5 g SCX cartridge (mega bond elut, Varian). Wash resin with methanol, then elute product with 2 M ammonia in methanol. Concentrate in vacuo, and chromatograph on silica gel, eluting with a gradient of 1-15% (2M ammonia in methanol) in CH2Cl2. Concentrate in vacuo. Dissolve the purified oil (115 mg, 38% isolated yield) in methanol, add solid NH4Cl (21.2 mg, 1 eq) and sonicate the solution at room temperature for 15 min. Concentrate in vacuo to provide the title compound: mass spectrum (ion spray): m/z=290.2 (M+1); Anal calculated for C17H28ClN3O.0.1H2O: Theory: C, 62.31; H, 8.67; N, 12.82. Found: C, 62.32; H, 8.78; N, 12.56.

Workup

  1. concentrationConcentrate in vacuo, and chromatograph on silica gel
  2. washeluting with a gradient of 1-15% (2M ammonia in methanol) in CH2Cl2
  3. concentrationConcentrate in vacuo
  4. dissolutionDissolve
  5. customthe purified oil (115 mg, 38% isolated yield) in methanol
  6. customsonicate the solution at room temperature for 15 min
  7. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-b80e1482e8ff451080e68bde3118c91e
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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