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

HRID 217785

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.[CH3:16][O:17][CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][NH:21][CH2:20][CH2:19][CH2:18][O:17][CH3:16])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 85 °C

Procedure

3-(4-bromophenyl)propyl methanesulfonate (418 g) and acetonitrile (2 L) were charged into reactor 1. 3-methoxypropylamine (305 g) and potassium carbonate (394 g) were added to reactor 1 and the mixture was warmed to 80-90° C. for 4-16 h. The mixture was analysed for completion (3-(4-bromophenyl)propyl methanesulfonate <0.5%). The reaction was cooled to 25° C. and the suspension was filtered to remove the white solids. The filtrate was concentrated to dryness on a rotary evaporator. The crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L) were charged into reactor 2. After phase separation, the organic layer was collected and washed with 1N HCl (2 L) until pH=4-5. After phase separation, the aqueous phase was basified by 2.5N NaOH solution to pH=9-10 and the resulting aqueous solution was used in the next step without further treatment.

Workup

temperatureThe reaction was cooled to 25° C.
filtrationthe suspension was filtered
customto remove the white solids
concentrationThe filtrate was concentrated to dryness on a rotary evaporator
customThe crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L)
additionwere charged into reactor 2
customAfter phase separation
customthe organic layer was collected
washwashed with 1N HCl (2 L) until pH=4-5
customAfter phase separation

Sources & evidence

ORD record: ord-a183de74b8264e66a58fed0d0b7f9435
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198285B2

Linked notes

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