Cyclopropylamine → HCID 21196049, compound

HRID 1066825Notes

Reaction equation

HRID 1066825 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[F:5][C:6]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:7]=1[CH2:8][O:9][CH2:10][C:11]#[C:12][CH2:13]Br>O1CCCC1.C(Cl)Cl>[CH:1]1([NH:4][CH2:13][C:12]#[C:11][CH2:10][O:9][CH2:8][C:7]2[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:6]=2[F:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 21195964HCID 21195964, compound

Product 1

HCID 21196049HCID 21196049, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of cyclopropylamine (1.10 ml, 15.8 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)but-2-ynyl bromide (530 mg, 1.58 mmol) in tetrahydrofuran (8 ml). The cloudy reaction mixture was stirred for about thrity minutes. The reaction mixture was then cooled to 0° C., and held at this temperature for about four hours, at which time no starting material remained, as determined by thin layer chromatography. The reaction mixture was diluted with methylene chloride (50 ml) and washed with 1 M potassium carbonate (10 ml). The organic fraction was dried over sodium sulfate. The solvents were removed in vacuo. The resulting oil was further purified by preparative high performance liquid chromatography, affording 362 mg (73%) of the title intermediate as a clear oil.

Workup

  1. customThe cloudy reaction mixture
  2. washwashed with 1 M potassium carbonate (10 ml)
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. customThe solvents were removed in vacuo
  5. customThe resulting oil was further purified by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-2b24ac98f9084eb3b2a6b92cc6271dba
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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