Triethylamine → HCID 59764404, compound

HRID 2046964Notes

Reaction equation

HRID 2046964 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, compoundHCID 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 (10 g, 38.5 mmol) in DCM (200 mL) and DMF (1 mL), was added thionyl chloride (9.17 g, 77 mmol) slowly via a syringe. The mixture was stirred for 3 hours, and concentrated to dryness. The obtained white solid, 2-chloro-4-isopropoxy-5-nitro-benzoyl chloride, was 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), was added 2-chloro-4-isopropoxy-5-nitro-benzoyl chloride (2 g, 7.2 mmol) dissolved in DCM (10 mL) slowly via syringe. The mixture was stirred at room temperature for 3 hours, and concentrated. The obtained solid was dissolved in ethyl acetate and washed with water and brine respectively. After evaporation of the solvent, the title compound was obtained as light yellow solid, and was directly used for the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-72e20210a80043a6aee90ca23f40e082
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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