4-Iodophenylacetonitrile → N-p-Benzeneacetonitrile menthanecarboxamide, (+)-

HRID 407531Notes

Reaction equation

HRID 407531 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][C@H:17]([CH3:19])[CH2:16][CH2:15][C@H:14]2[CH:20]([CH3:22])[CH3:21])=[O:12])=[CH:6][CH:5]=1)#[N:2].C([C@@H]1CC[C@@H](C)C[C@@H]1C(N)=O)(C)C.C(CC1C=CC(I)=CC=1)#N>>[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C@H:13]2[CH2:18][C@H:17]([CH3:19])[CH2:16][CH2:15][C@H:14]2[CH:20]([CH3:22])[CH3:21])=[O:12])=[CH:6][CH:5]=1)#[N:2]

Participants

4

Reactant 3

HCID 1428664-IodophenylacetonitrileHCID 44467796N-p-Benzeneacetonitrile menthanecarboxamideHCID 59253418(1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide

Product 1

HCID 46174464N-p-Benzeneacetonitrile menthanecarboxamide, (+)-

Procedure

N-[4-(cyanomethyl)phenyl]-(1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide was prepared as described above for the preparation of the N-[4-(cyanomethyl)phenyl]-(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide isomer, i.e., by coupling the (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide prepared in steps A to C above with 4-(cyanomethyl)phenyl iodide. The (1S,2S,5R)-material (neoisomer) has the following properties with structure confirmed by obtaining an X-ray crystal structure of a sample crystallized from hexane/ethyl acetate.

Workup

  1. customby obtaining an X-ray crystal structure of a sample
  2. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-dfbe441642734b90ab4929d3eee94f83
Source dataset
uspto-grants-2014_06
Patent number
US08754259B2

Reaction notes

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