Triethylamine → t-Butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate

HRID 384845Notes

Reaction equation

HRID 384845 reaction equation
Cl.C(N=C=NCCCN(C)C)C.Cl.[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][C:23]=1[O:30][CH3:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([C:45](O)=[O:46])[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>C(Cl)Cl>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([C:45](=[O:46])[NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:23]([O:30][CH3:31])[CH:24]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162477591-[4-(Benzyloxy)-3-methoxyphenyl]methanamine--hydrogen chloride (1/1)

Product 1

HCID 66587122t-Butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylateYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12.5 g) was added to a mixture of 4-benzyloxy-3-methoxy benzylamine hydrochloride (14.0 g), 1-(t-butoxycarbonyl)-piperidine-4-carboxylic acid (11.5 g), triethylamine (14.0 ml) and methylene chloride (300 ml). After stirring the reaction mixture at room temperature for 20 hours, the mixture was washed with saturated ammonium chloride aqueous solution and then saturated brine, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 16.3 g of t-butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.

Workup

  1. washthe mixture was washed with saturated ammonium chloride aqueous solution
  2. dry with materialsaturated brine, the organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient)

Sources & evidence

ORD record
ord-905b62f0ad214204980c60768b785b3a
Source dataset
uspto-grants-2013_02
Patent number
US08367835B2

Reaction notes

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