Acetic Anhydride → HCID 68860839, compound

HRID 2110829Notes

Reaction equation

HRID 2110829 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32].C(OCC)(=O)C>O1CCCC1.CCCCCC>[C:31]([N:7]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH2:10]1)[CH2:6][C:5]1[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 68862824HCID 68862824, compound

Product 1

HCID 68860839HCID 68860839, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-(N-(4-chlorobenzyl)aminomethyl)-1-t-butoxycarbonylpiperidine(300 mg, 0.89 mmol) and triethylamine (180 mg, 1.78 mmol) in tetrahydrofuran (15 mL) stirring at room temperature under argon, was added acetic anhydride (109 mg, 1.07 mmol) in a single portion. After 16 h the mixture was evaporated under vacuum. Column chromatography (silica gel, 65% ethyl acetate in hexane) provided 4-(N-acetyl-N-(4-chlorobenzyl)aminomethyl)-1-t-butoxycarbonylpiperidine (309 mg, 91% yield). TLC Rf=0.30, 65% ethyl acetate in hexane.

Workup

  1. customAfter 16 h the mixture was evaporated under vacuum

Sources & evidence

ORD record
ord-6c44dc135e7d455b95b462787b69b07e
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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