Hydrochloric Acid → HCID 117992135, compound

HRID 531056Notes

Reaction equation

HRID 531056 reaction equation
C1(C)C=CC=CC=1.C[Al](C)C.[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][CH2:29][CH2:30][CH2:31][C:32]2[N:42]=[CH:41][CH:40]=[CH:39][C:33]=2[C:34](OCC)=[O:35])[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>O.ClCCl>[O:35]=[C:34]1[C:33]2[CH:39]=[CH:40][CH:41]=[N:42][C:32]=2[CH2:31][CH2:30][CH2:29][N:28]1[CH:25]1[CH2:24][CH2:23][N:22]([C:20]([O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:21])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 16682925TrimethylaluminumHCID 117992285HCID 117992285, compound

Product 1

HCID 117992135HCID 117992135, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 2 M toluene solution (14.6 mL) of trimethylaluminum was added at 0° C. to a mixture of ethyl 2-(3-((1-((benzyloxy)carbonyl)piperidin-4-yl)amino)propyl)nicotinate (2.4 g) and dichloromethane (60 mL), and the resultant mixture was stirred at room temperature for 36 hours. Water was added to the reaction mixture, and then, the mixture was neutralized by the addition of hydrochloric acid. The organic layer was separated, and then, the aqueous layer was subjected to extraction with dichloromethane. Combined organic layers were washed with water and saturated saline and dried over sodium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol/dichloromethane) to obtain the title compound (1.2 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was subjected to extraction with dichloromethane
  3. washCombined organic layers were washed with water and saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-ef78066331644e8a83191a549c7fe004
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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