Diethylamine → N,N-dimethyl-4-(2-fluoro-5-bromobenzyloxy)butylamine

HRID 1066830Notes

Reaction equation

HRID 1066830 reaction equation
[CH2:1]([NH:3][CH2:4]C)C.[F:6][C:7]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:8]=1[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14]Br>O1CCCC1.C(Cl)Cl>[CH3:1][N:3]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][C:8]1[CH:16]=[C:17]([Br:20])[CH:18]=[CH:19][C:7]=1[F:6])[CH3:4]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 21196139HCID 21196139, compound

Product 1

HCID 21196124N,N-dimethyl-4-(2-fluoro-5-bromobenzyloxy)butylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethylamine (17.6 ml, 35.3 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)butyl bromide (1.2 g, 3.53 mmol) in tetrahydrofuran (18 ml). The resulting mixture was stirred at ambient temperature for about 18 hours. The reaction mixture was diluted with methylene chloride and washed with saturated sodium bicarbonate. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The desired title intermediate was further purified by high performance liquid chromatography.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. extractionThe aqueous fraction was back extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed in vacuo
  5. customThe desired title intermediate was further purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-ffa301ccf12f48d99f0b6e2c31eb9711
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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