Sodium Iodide → N-(t-butyl)-4-(2-fluoro-5-bromobenzyloxy)butylamine

HRID 1066833Notes

Reaction equation

HRID 1066833 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9]Br.[I-].[Na+].[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.C(Cl)Cl>[C:18]([NH:22][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:2]=1[F:1])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6385Tert-ButylamineHCID 21196139HCID 21196139, compound

Product 1

HCID 21196157N-(t-butyl)-4-(2-fluoro-5-bromobenzyloxy)butylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(2-fluoro-5-bromobenzyloxy)butyl bromide (400 mg, 1.18 mmol) in tetrahydrofuran (6 ml) was treated with sodium iodide (242 mg, 1.6 mmol). The resulting mixture was stirred at ambient temperature. After 1.5 hours, the sodium bromide was removed by filtration, and the filtrate concentrated. The residue was treated with a tetrahydrofuran solution of tert-butylamine (1.24 ml, 11.8 mmol). The progress of the reaction was monitored by thin layer chromatography. The resulting mixture was stirred for about 19 hours at ambient temperature. The reaction mixture was diluted with methylene chloride, and washed with saturated sodium bicarbonate. The organic fraction was dried over sodium sulfate and the solvents were removed in vacuo. The desired title intermediate was further purified by radial chromatography.

Workup

  1. customthe sodium bromide was removed by filtration
  2. concentrationthe filtrate concentrated
  3. stirringThe resulting mixture was stirred for about 19 hours at ambient temperature
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic fraction was dried over sodium sulfate
  6. customthe solvents were removed in vacuo
  7. customThe desired title intermediate was further purified by radial chromatography

Sources & evidence

ORD record
ord-f279e34001da4ea3964a7a0056214e03
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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