Dimethylamine → HCID 178437759, compound

HRID 241076

Reaction equation

HRID 241076 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH:5]([C:7]1[N:16]=[C:15]([OH:17])[C:14]2[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11][CH2:10][C:9]=2[N:8]=1)[CH3:6].ClC(C)C#N>>[CH3:1][N:2]([CH3:3])[CH:5]([C:7]1[N:16]=[C:15]([OH:17])[C:14]2[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11][CH2:10][C:9]=2[N:8]=1)[CH3:6]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 5192252-ChloropropionitrileHCID 178456123HCID 178456123, compound

Product 1

HCID 178437759HCID 178437759, compoundYield 96%

Conditions

Temperature
80 °C

Procedure

To a solution of dimethylamine (2M solution in tetrahydrofuran, 4.0 mL, 8.0 mmol) was added 2-(1-chloroethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-ol (synthesized according to the method of reagent preparation 18 using 2-chloropropionitrile in step 1) (50 mg, 0.21 mmol) and the reaction mixture was stirred in a sealed tube for 16 hours at 80° C. After cooling to room temperature the reaction mixture was concentrated and the residue was partitioned between brine (50 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated to give 2-[1-(dimethylamino)ethyl]-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-ol (50 mg, 96%). MS (EI) for C14H23N3O: 250 (MH+).

Workup

  1. customsynthesized
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. concentrationwas concentrated
  4. customthe residue was partitioned between brine (50 mL) and ethyl acetate (50 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-324e2d1ff11845368ba33ed05f09b953
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Linked notes

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