Benzoyl chloride → Allyl 4-((2-benzamidoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate

HRID 59787Notes

Reaction equation

HRID 59787 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:8][CH2:7]1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:36]([NH:2][CH2:3][CH2:4][N:5]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:10][CH2:11]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 121410349Allyl 4-((2-aminoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate hydrochloride

Product 1

HCID 121410296Allyl 4-((2-benzamidoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

Allyl 4-((2-aminoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate hydrochloride obtained in Step 2 was suspended in dichloromethane (4 mL/mmol), the suspension was cooled to −15° C. and DIPEA (2.2 equiv) followed by benzoyl chloride (1.05 equiv) were added dropwise over 5 minutes. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. After 2 h TLC revealed no presence of starting material. The reaction mixture was diluted with EtOAc (10 mL/mmol of starting material), washed with 1 M NaOH (2×), water (2×) and brine (2×) and dried over anhydrous MgSO4. After filtration of the drying agent the solvent was stripped off and the crude product was purified by column chromatography.

Workup

  1. additionwere added dropwise over 5 minutes
  2. customThe cooling bath was removed
  3. temperatureto warm to ambient temperature
  4. additionThe reaction mixture was diluted with EtOAc (10 mL/mmol of starting material)
  5. washwashed with 1 M NaOH (2×), water (2×) and brine (2×)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationAfter filtration of the drying agent the solvent
  8. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-14a48e7073404c54acd9c489ddbd544f
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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