Hydrochloric Acid → HCID 58577103, compound

HRID 511118Notes

Reaction equation

HRID 511118 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][N:24]=1.Cl>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][N:24]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58577103HCID 58577103, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (440 mg; 2.2 mmol), triethylamine (420 μL; 3.0 mmol) and 2-chloro-4-methyl-5-nitro-pyridine (346 mg; 2.0 mmol) is irradiated in a mono-mode microwave oven for 10 hours at 120° C. The mixture is then cooled to room temperature, water is added (5 mL) and the pH is adjusted to pH 4-5 by addition of aq. 1N hydrochloric acid. After extraction with dichloromethane (2×10 mL), the combined organic layers are dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:ethyl acetate 1:0; 12:1; 2:1) to afford the desired product (480 mg; 1.43 mmol).

Workup

  1. customis irradiated in a mono-mode microwave oven for 10 hours at 120° C
  2. extractionAfter extraction with dichloromethane (2×10 mL)
  3. dry with materialthe combined organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue obtained
  7. customis finally purified by column chromatography on silica gel (dichloromethane:ethyl acetate 1:0; 12:1; 2:1)

Sources & evidence

ORD record
ord-6f17efa5d8a84fd3ab0f63138fd33911
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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