3-Methoxypropylamine → 3-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

HRID 217776Notes

Reaction equation

HRID 217776 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:22][O:23][CH2:24][CH2:25][CH2:26][NH2:27]>CC#N>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][NH:27][CH2:26][CH2:25][CH2:24][O:23][CH3:22])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 196884663-(4-Bromophenyl)propyl methanesulphonate

Product 1

HCID 666785803-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the product of step (i) (272 g, 0.93 mol), K2CO3 (256 g, 1.86 mol), methoxypropylamine (199 g, 2.22 mol) in MeCN (1.5 L) was stirred at 80-90° C. under N2 atmosphere for 16 hour. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated to remove MeCN. MTBE (1 L) and H2O (1 L) were charged to the resulting mixture and washed with aqueous 1N—HCl (1 L). The aqueous phase was collected and basified by aqueous 2.5N—NaOH to pH=9-10, to afford the subtitle compound (ii) in solution, which was used for next step directly.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customto remove MeCN
  5. additionMTBE (1 L) and H2O (1 L) were charged to the resulting mixture
  6. washwashed with aqueous 1N—HCl (1 L)
  7. customThe aqueous phase was collected

Sources & evidence

ORD record
ord-bf34091038c54a478c272f01df69e410
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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