N-Ethyl-N-methylcarbamoyl chloride → HCID 44455199, compound

HRID 1920772Notes

Reaction equation

HRID 1920772 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH:13]3[CH2:15][CH2:14]3)[CH2:9]2)=[CH:4][CH:3]=1.[CH2:16]([N:18]([CH3:22])[C:19](Cl)=[O:20])[CH3:17]>>[CH3:22][N:18]([CH2:16][CH3:17])[C:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:9]2)=[CH:4][CH:3]=1)=[O:20]

Participants

3

Reactant 2

HCID 11240471N-Ethyl-N-methylcarbamoyl chlorideHCID 67493078HCID 67493078, compound

Product 1

HCID 44455199HCID 44455199, compoundYield 50%

Procedure

7-Hydroxy-N-cyclopropylmethyl-1,2,3,4-tetrahydroisoquinoline (9) was mixed homogeneously with N-ethyl-N-methyl-carbamoyl chloride (10a) and carried out step (f-2). Purified on a silica gel column (DCM/MeOH=10:1) gave cyclopropylmethyl- and N-Ethyl-N-methyl amino-containing 7-(N-Methyl-N-ethyl-carbamoyloxy)-N-cyclopropylmethyl-1,2,3,4-tetrahydroisoquinoline (12a) (Yield 50%). 1H NMR (300 MHz, CDCl3) (NMR, Varian Gemini): δ 7.06 (d, J=8 Hz, 1H, Aryl H); 6.84 (s, 1H, Aryl H); 6.81 (s, 1H, Aryl H): 3.71 (s, 2H, Ph-CH2—N); δ 3.44, 3.39 (dd, J=7 Hz, 2H, CH3—N—CH2CH3); 3.03-2.75 (m, 7H, CH3—N—CH2—CH3, Ph-CH2—CH2—N); 2.42 (d, J=6 Hz, 2H, N—CH2); 1.24-1.17 (m, 3H, —CH3); 1.14-0.94 (q, J=7 Hz, 1H); 0.58-0.52 (m, 2H); 0.19-0.14 (m, 2H); IR (KBr): ν cm−1=2924, 1715. Fast Atom Bombardment Mass Spectrometry (FABMS) m/z: 289 (M+1) (C17H24N2O2).

Workup

  1. customPurified on a silica gel column (DCM/MeOH=10:1)
  2. customgave cyclopropylmethyl- and N-Ethyl-N-methyl amino-

Sources & evidence

ORD record
ord-2b6943175d0e4d99af2295418a44bfa2
Source dataset
uspto-grants-2012_05
Patent number
US08173648B2

Reaction notes

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