Phenylacetyl chloride → N-[4-(methoxymethyl)-1-(1-methylethyl)-4-piperidinyl]-N-phenylbenzeneacetamide hydrochloride

HRID 2049435Notes

Reaction equation

HRID 2049435 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][N:7]([CH:10]([CH3:12])[CH3:11])[CH2:6][CH2:5]1.[C:20]1([CH2:26][C:27]([Cl:29])=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[ClH:29].[CH3:1][O:2][CH2:3][C:4]1([N:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:27](=[O:28])[CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][CH2:8][N:7]([CH:10]([CH3:12])[CH3:11])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 233390404-(Methoxymethyl)-N-phenyl-1-(propan-2-yl)piperidin-4-amine

Product 1

HCID 20334079N-[4-(methoxymethyl)-1-(1-methylethyl)-4-piperidinyl]-N-phenylbenzeneacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred mixture of 5.5 parts of 4-(methoxymethyl)-1-(1-methylethyl)-N-phenyl-4-piperidinamine in 56 parts of benzene is added dropwise a solution of 13.8 parts of benzeneacetyl chloride in 45 parts of benzene at 26°-32° C. Upon completion, stirring is continued first for one hour at 26°-32° C. and further for 3.60 hours at 38°-55° C. After cooling, the precipitated product is filtered off and converted into the hydrochloride salt in a mixture of 2-propanol and 2-propanone (5:1 by volume). The salt is filtered off and dissolved in absolute ethanol. After standing for 72 hours at room temperature, the precipitated product is filtered off, washed with a small amount of 2-propanone and dried, yielding 1.05 parts of N-[4-(methoxymethyl)-1-(1-methylethyl)-4-piperidinyl]-N-phenylbenzeneacetamide hydrochloride; mp. 249.1° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated product is filtered off
  3. additionconverted into the hydrochloride salt in a mixture of 2-propanol and 2-propanone (5:1 by volume)
  4. filtrationThe salt is filtered off
  5. dissolutiondissolved in absolute ethanol
  6. waitAfter standing for 72 hours at room temperature
  7. filtrationthe precipitated product is filtered off
  8. washwashed with a small amount of 2-propanone
  9. customdried

Sources & evidence

ORD record
ord-ca2a7f4addfc4300ac2eaf3c3497a321
Source dataset
uspto-grants-1980_04
Patent number
US04197303

Reaction notes

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