Chloroform → 1-(4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)-N,N-dimethylethanamine

HRID 241077Notes

Reaction equation

HRID 241077 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]([C:5]1[N:14]=[C:13](O)[C:12]2[CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4].C(Cl)(Cl)[Cl:20]>P(Cl)(Cl)(Cl)=O>[Cl:20][C:13]1[C:12]2[CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][CH2:8][C:7]=2[N:6]=[C:5]([CH:3]([N:2]([CH3:18])[CH3:1])[CH3:4])[N:14]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 178437759HCID 178437759, compound

Product 1

HCID 866478331-(4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)-N,N-dimethylethanamineYield 85%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 2-[1-(dimethylamino)ethyl]-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-ol (50 mg, 0.20 mmol) in a mixture of chloroform (1.5 mL) and phosphorous oxychloride (0.5 mL) was heated to reflux for 90 minutes. After cooling to room temperature the reaction mixture was concentrated and the residue was partitioned between saturated aqueous sodium bicarbonate (20 mL) and ethyl acetate (20 mL). The mixture was stirred for 15 minutes and pH was maintained above 7 by the addition of solid sodium bicarbonate. The organic layer was separated and washed with water (10 mL) and brine, dried over sodium sulfate, filtered and concentrated to give 1-(4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)-N,N-dimethylethanamine (46 mg, 85%). MS (EI) for C14H22ClN3: 268 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 minutes
  3. concentrationwas concentrated
  4. customthe residue was partitioned between saturated aqueous sodium bicarbonate (20 mL) and ethyl acetate (20 mL)
  5. temperaturepH was maintained above 7 by the addition of solid sodium bicarbonate
  6. customThe organic layer was separated
  7. washwashed with water (10 mL) and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-480b916fd01f4988ba659c8d74d5cdaa
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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