N,N-diethyl-2-butyne-1,4-diamine → N-(4-diethylamino-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide hydrochloride

HRID 973991Notes

Reaction equation

HRID 973991 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[CH2:4][C:5]#[C:6][CH2:7][NH2:8])[CH3:2].[Cl:11][C:12]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](Cl)=[O:14]>C1C=CC=CC=1>[ClH:11].[CH2:1]([N:3]([CH2:9][CH3:10])[CH2:4][C:5]#[C:6][CH2:7][NH:8][C:13](=[O:14])[C:12]([Cl:11])([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12259571N,N-diethyl-2-butyne-1,4-diamineHCID 197755142-Chloro-2-cyclohexyl-2-phenylacetyl chloride

Product 1

HCID 19775490N-(4-diethylamino-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide hydrochlorideYield 92.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 4-diethylamino-2-butynylamine (0.14 g) in benzene (2.5 ml) was added dropwise to a solution of 2-chloro-2-cyclohexyl-2-phenylacetyl chloride (0.27 g) in benzene (2.5 ml below 25° C. After being stirred at room temperature for 19.5 hours, the resulting precipitates were collected by filtration and recrystallized from a mixture of acetone and diethyl ether to give N-(4-diethylamino-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide hydrochloride (0.19 g).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from a mixture of acetone and diethyl ether

Sources & evidence

ORD record
ord-ab64516c28dc481783cc8c7ef0788c98
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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