N-Ethyl-N-methylcarbamoyl chloride → HCID 44455327, compound

HRID 1920771Notes

Reaction equation

HRID 1920771 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][C:13]#[CH:14])[CH2:9]2)=[CH:4][CH:3]=1.[CH2:15]([N:17]([CH3:21])[C:18](Cl)=[O:19])[CH3:16]>>[CH3:21][N:17]([CH2:15][CH3:16])[C:18]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][C:13]#[CH:14])[CH2:9]2)=[CH:4][CH:3]=1)=[O:19]

Participants

3

Reactant 2

HCID 11240471N-Ethyl-N-methylcarbamoyl chlorideHCID 866380911018448-54-8

Product 1

HCID 44455327HCID 44455327, compoundYield 50%

Procedure

7-Hydroxy-N-propargyl-1,2,3,4-tetrahydroisoquinoline (8) was mixed homogeneously with N-ethyl-N-methyl-carbamoyl chloride (10a) and then carried out step (f-1). Purified on a silica gel column (EtOAc/n-hexane=2:1) gave propargyl- and N-Ethyl-N-methyl amino-containing 7-(N-Methyl-N-ethylcarbamoyloxy)-N-propargyl-1,2,3,4-tetrahydroisoquinoline (11a) (Yield 50%). 1H NMR (300 MHz, CDCl3) (NMR, Varian Gemini): δ 7.08 (d, J=8 Hz, 1H, Aryl H), 6.88 (d, J=7 Hz, 1H, Aryl H); 6.80 (s, 1H, Aryl H), 3.76 (s, 2H, Ph-CH2—N), 3.50 (d, J=2 Hz, 2H, N—CH2—CCH), 3.42 (q, J=7 Hz, 2H, N—CH2—CH3), 3.04-2.81 (m, 7H, N—CH3, Ph-CH2—CH2—N), 2.28-2.26 (m, 1H, C≡CH), 1.25-1.15 (m, 3H, N—CH2—CH3); IR (KBr): ν cm−1=3300, 2923, 1715. Fast Atom Bombardment Mass Spectrometry (FABMS) m/z: 273 (M+1) (C16H20N2O2).

Workup

  1. customPurified on a silica gel column (EtOAc/n-hexane=2:1)
  2. customgave propargyl- and N-Ethyl-N-methyl amino-

Sources & evidence

ORD record
ord-809dd29927b44ac1af985a50c75fc0eb
Source dataset
uspto-grants-2012_05
Patent number
US08173648B2

Reaction notes

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