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

Participants

Reaction Steps

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).

Provenance & Evidence