Triethylamine → HCID 69955951, compound

HRID 478904Notes

Reaction equation

HRID 478904 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:21]([O:28][C:29](=[O:32])[CH2:30]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.CCOC(C)=O>[CH2:21]([O:28][C:29](=[O:32])[CH2:30][N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 317384-BenzylpiperidineHCID 62576Benzyl bromoacetate

Product 1

HCID 69955951HCID 69955951, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-benzylpiperidine (6) (2.00 g, 11.41 mmol) in dichloromethane (20 mL) at 0° C. was added triethylamine (1.59 mL, 11.41 mmol), followed by benzyl-2-bromoacetate (1.81 mL, 11.41 mmol). After 10 minutes a white precipitate was observed. The reaction mixture was allowed to warm to room temperature. After 45 minutes the reaction mixture was condensed to dryness in vacuo, redissolved in EtOAc (50 mL), the organic phase washed with saturated aqueous sodium hydrogen carbonate (50 mL), and saturated brine (50 mL). The organic phase was dried (MgSO4) and condensed to dryness to give (4-benzylpiperidin-1-yl)acetic acid benzyl ester (3.69 g, 100%) as a pale yellow oil:

Workup

  1. waitAfter 45 minutes the reaction mixture was
  2. customcondensed to dryness in vacuo
  3. washthe organic phase washed with saturated aqueous sodium hydrogen carbonate (50 mL), and saturated brine (50 mL)
  4. customThe organic phase was dried
  5. custom(MgSO4) and condensed to dryness

Sources & evidence

ORD record
ord-44a0e63536c64ac588761ada43a4f048
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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