Hydrochloric Acid → [(2-Bromophenyl)methyl](cyclopropylmethyl)amine

HRID 1631154Notes

Reaction equation

HRID 1631154 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH2:6][NH:7][CH:8]1[CH2:10][CH2:9]1.I[CH3:16].Cl>O1CCCC1>[Br:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH2:6][NH:7][CH2:8][CH:10]1[CH2:9][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20120601N-[(2-bromophenyl)methyl]cyclopropanamine

Product 1

HCID 28431311[(2-Bromophenyl)methyl](cyclopropylmethyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

53 mg of sodium hydride in 3 ml of tetrahydrofuran are added to 300 mg of (2-bromobenzyl)cyclopropylamine in 2 ml of tetrahydrofuran with ice-cooling. 207 μl of iodomethane are subsequently added, and the mixture is heated at 600 for 1 h. The mixture is allowed to cool and poured onto 20 g of ice and 5 ml of 1N hydrochloric acid, washed 4 times with 10 ml of ethyl acetate each time, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness.

Workup

  1. temperaturecooling
  2. temperaturethe mixture is heated at 600 for 1 h
  3. temperatureto cool
  4. washwashed 4 times with 10 ml of ethyl acetate each time
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-20c744233e1440fb86f58e54d4f462bd
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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