Tert-Butylamine → 7-(Tert-butylamino-methyl)-6-chloro-chroman-4-one

HRID 747045Notes

Reaction equation

HRID 747045 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Br[CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:25])[CH2:20][CH2:21][O:22]2)=[CH:17][C:16]=1[Cl:26]>C(Cl)Cl>[C:1]([NH:5][CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:25])[CH2:20][CH2:21][O:22]2)=[CH:17][C:16]=1[Cl:26])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 690773757-Bromomethyl-6-chlorochroman-4-one

Product 1

HCID 690782167-(Tert-butylamino-methyl)-6-chloro-chroman-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of tert-butylamine (7.3 g, 99.78 mmol) and Et3N (10.1 g, 99.78 mmol) in anhydrous CH2Cl2 (50 mL) was added a solution of 7-bromomethyl-6-chloro-chroman-4-one (25 g, 90.71 mmol) in CH2Cl2 (150 mL) dropwise. Stirring was continued for 16 h. The mixture was concentrated, taken up in H2O, acidified with 10% HCl until pH 1, and extracted with Et2O (discarded). The acidic aqueous layer was neutralized with 5 N NaOH, and extracted with CH2Cl2 (3×). The combined extracts were dried over MgSO4, concentrated to give a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with Et2O (discarded)
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-4f16f4fb490648db99530ae178c09921
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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