N,N-Dimethylaniline → HCID 19748194, compound

HRID 484389Notes

Reaction equation

HRID 484389 reaction equation
Br[CH2:2][CH2:3][CH2:4]N.[N:6]1[C:11](C)=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14].CN1CC[O:19]CC1.C[N:23]([CH3:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26]C=1.N1C(C)=CC=CC=1C>C(O)(C)C.ClC1C=CC=CC=1.ClC(Cl)(Cl)C.C1(C)C=CC=CC=1.C(O)CCC.C(N(CC)CC)C>[CH:2]1[C:8]2[CH:7]3[N:6]([C:26](=[O:19])[C:27]4[CH2:28][CH2:29][CH2:24][NH:23][C:30]=4[CH2:14]3)[CH2:11][CH2:10][C:9]=2[CH:13]=[CH:4][CH:3]=1

Participants

12

Reactant 5

HCID 949N,N-DimethylanilineHCID 79372,6-Lutidine2×HCID 79532,4,6-TrimethylpyridineHCID 79724-MethylmorpholineHCID 787023-Bromopropylamine

Product 1

HCID 19748194HCID 19748194, compound

Reagents, catalysts & solvents 6

HCID 2631-ButanolSolventHCID 1140TolueneSolventHCID 3776IsopropanolSolventHCID 62781,1,1-TrichloroethaneSolventHCID 7964ChlorobenzeneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Typically a compound of formula (4) is dissolved in an appropriate solvent, such as isopropanol, chlorobenzene, 1,1,1-trichloroethane, toluene, or preferably n-butanol, and about 1-2 molar equivalents, preferably about 1.1 molar equivalents, of the appropriate 3-halopropylamine added, preferably 3-bromopropylamine as its hydrobromide salt, followed by about 1.5 to 4 molar equivalents, preferably about 2.2 molar equivalents, of a tertiary base (such as triethylamine, collidine, N-methylmorpholine, N,N-dimethylaniline or 2,6-lutidine, preferably 2,6-lutidine). The mixture is heated to a temperature of about 80° C. to reflux temperature, preferably about reflux temperature, for about 20 minutes to 4 hours, preferably about 1 hour. A (±)-5,6,9,10,11,12,13,13a-octahydroisoquino[2,1-g][1,6]naphthyridin-8-one derivative, a compound of formula (5), is isolated by conventional means, and purified for example by crystallization from aqueous methanol.

Workup

  1. additionadded
  2. temperatureto reflux temperature
  3. temperaturepreferably about reflux temperature
  4. waitfor about 20 minutes to 4 hours
  5. custompreferably about 1 hour

Sources & evidence

ORD record
ord-faf63c9cef1d436ea230eb20fa688564
Source dataset
uspto-grants-1993_07
Patent number
US05231181

Reaction notes

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