Toluene → HCID 23324842, compound

HRID 1380960Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][O:22][CH3:23])([NH:14][C:15]2[CH:20]=CC=CC=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:25][CH2:26][C:27](Cl)=O.C(N(CC)CC)C.[OH-:37].[Na+].[C:39]1(C)C=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([CH2:21][O:22][CH3:23])([N:14]([O:25][CH2:26][C:27]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:15](=[O:37])[CH3:20])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 5

HCID 1140Toluene2×

HCID 8471Triethylamine

HCID 14798Sodium Hydroxide

HCID 96623Methoxyacetyl chloride2×

HCID 30477241-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amine

Product 1

HCID 23324842HCID 23324842, compound

Procedure

A mixture of 9.75 g of 1-benzyl-4-methoxymethyl-4-anilinopiperidine, 3 g of methoxyacetyl chloride, 9 ml of triethylamine and 80 ml of toluene is stirred at ambient conditions for 4 days. An additional 3 g of methoxyacetyl chloride is added, stirred for 1 day and left to stand for three days. To the reaction mixture, 22 ml of 10% sodium hydroxide and 80 ml toluene are added with stirring. The organic layer is separated, washed five times with 50 ml portions of water, dried over sodium sulfate and flash evaporated to give an oil. The oil is purified using a Waters Associates Prep LC/System 500, and a PrepPAK-500/SILICA column (30% hexane in ethyl acetate) to give 8.12 g of 1-benzyl-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine.

Workup

stirringstirred for 1 day
waitleft
waitto stand for three days
stirringwith stirring
customThe organic layer is separated
washwashed five times with 50 ml portions of water
dry with materialdried over sodium sulfate and flash
customevaporated
customto give an oil
customThe oil is purified

Sources & evidence

ORD record: ord-8955732781184e1caeeafcefbe153f06
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04584303

Reaction notes

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