Pyridine → 4-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl ester

HRID 2221074Notes

Reaction equation

HRID 2221074 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][Cl:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 740895-Chlorovaleryl chlorideHCID 178466404-Amino-1-N-Cbz-piperidine

Product 1

HCID 233699784-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl esterYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Amino-piperidine-1-carboxylic acid benzyl ester (12.0 g) in dichloromethane (100 mL) was added to pyridine (7.2 mL). The solution was cooled to 0° C. then 5-chlorovaleryl chloride (7.3 g) was added drop wise to the reaction. The reaction was warmed to room temperature. After 5 hours the reaction was diluted with dichloromethane and washed with water (1×), saturated aqueous copper sulfate (2×), and water (1×). The organic extracts were dried and evaporated. The resulting solids were suspended in ether, filtered, and then placed under high vacuum to give the title compound as a white solid (15.6 g). Rf=0.60 in ethyl acetate.

Workup

  1. customwise to the reaction
  2. temperatureThe reaction was warmed to room temperature
  3. washwashed with water (1×), saturated aqueous copper sulfate (2×), and water (1×)
  4. customThe organic extracts were dried
  5. customevaporated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d68677dc353946c798c19d90c4cadd91
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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