Triethylamine → HCID 59764404, compound

HRID 386766Notes

Reaction equation

HRID 386766 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.ClC1C=C(OC(C)C)C([N+]([O-])=O)=CC=1C(Cl)=O>C(Cl)Cl.CN(C=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH:35][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:10][C:2]=2[Cl:1])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 12682914-Amino-1-Boc-piperidineHCID 45480464HCID 45480464, compound2×HCID 86621732HCID 86621732, compound

Product 1

HCID 59764404HCID 59764404, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-chloro-4-isopropoxy-5-nitro-benzoic acid (Intermediate 8, 10 g, 38.5 mmol) in DCM (200 mL) and DMF (1 mL), is slowly added thionyl chloride (9.17 g, 77 mmol) via a syringe. The mixture is stirred for 3 hours, and is then concentrated to dryness. The obtained white solid, 2-chloro-4-isopropoxy-5-nitro-benzoyl chloride, is dried under vacuum. To a mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.44 g, 7.2 mmol) and triethylamine (3 mL, 21.6 mmol) in DCM (100 mL), is slowly added 2-chloro-4-isopropoxy-5-nitro-benzoyl chloride (2 g, 7.2 mmol) dissolved in DCM (10 mL) via syringe. The mixture is stirred at room temperature for 3 hours, and then is concentrated. The obtained solid is dissolved in ethyl acetate and is washed with water and brine respectively. After evaporation of the solvent, the title compound is obtained as light yellow solid, and is directly used for the next step without further purification.

Workup

  1. concentrationis then concentrated to dryness
  2. dry with materialThe obtained white solid, 2-chloro-4-isopropoxy-5-nitro-benzoyl chloride, is dried under vacuum
  3. stirringThe mixture is stirred at room temperature for 3 hours
  4. concentrationis concentrated
  5. dissolutionThe obtained solid is dissolved in ethyl acetate
  6. washis washed with water and brine respectively
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-20430e8e4b21452baf7b2ef3393cdfaf
Source dataset
uspto-grants-2013_02
Patent number
US08372858B2

Reaction notes

Loading…