Triethylamine → 7-(4-Benzamidopiperidinoacetyl)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene

HRID 1730360Notes

Reaction equation

HRID 1730360 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH3:16])=[C:9]([C:12](=[O:15])[CH2:13]Br)[CH:10]=2)[C:5]([CH3:18])([CH3:17])[CH:4]([CH3:19])[CH2:3]1.[C:21]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CCO>[C:21]([NH:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:18])([CH3:17])[CH:4]([CH3:19])[CH2:3][C:2]3([CH3:20])[CH3:1])=[CH:7][C:8]=2[CH3:16])=[O:15])[CH2:32][CH2:31]1)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118120N-4-PiperidylbenzamideHCID 214306251,1,3,4,4,6-Hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 214306217-(4-Benzamidopiperidinoacetyl)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthaleneYield 24.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,1,3,4,4,6-hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene (7 g.), 4-benzamidopiperidine (4.27 g.) and triethylamine (3.5 g.) was refluxed in100 ml. EtOH for 2 hours. The resulting yellow solution was cooled, whereupon the product crystallised. This was recrystallised twice from EtOH/water to give the title compound (2.3 g.) as a pale yellow solid, m.p. 153°(dec.). Analysis Calculated for C30H40N2O2 ; C, 78.22%; H, 8.75%; N, 6.08%. Found: C, 78.29%; H, 8.92%; N, 6.14%.

Workup

  1. temperaturewas refluxed in100 ml
  2. temperatureThe resulting yellow solution was cooled, whereupon the product
  3. customcrystallised
  4. customThis was recrystallised twice from EtOH/water

Sources & evidence

ORD record
ord-1afb6b98244f4aabb8679724746b5ab4
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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