Dimethylamine → 1-(4-Chlorophenyl)-N4,N4-dimethylbutane-1,4-diamine

HRID 423075Notes

Reaction equation

[CH3:1][NH:2][CH3:3].CS(O[CH2:9][CH2:10][CH2:11][CH:12]([NH:20]C(OC(C)(C)C)=O)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=O)=O>C1COCC1>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH:12]([NH2:20])[CH2:11][CH2:10][CH2:9][N:2]([CH3:3])[CH3:1])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Dimethylamine (84 mg, 1.85 mmol) and 4-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate (Intermediate 56) (700 mg, 1.85 mmol) were dissolved in THF (10 mL) and sealed into a microwave tube. The reaction was heated to 120° C. for 40 minutes in the microwave reactor and cooled to room temperature. The reaction mixture was concentrated and then dissolved in DCM (10.00 mL) and TFA (2 mL). The reaction was stirred at 20° C. for 2 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 3.5N ammonia/MeOH and pure fractions were evaporated to dryness to afford 1-(4-chlorophenyl)-N4,N4-dimethylbutane-1,4-diamine (366 mg, 87%) as a yellow gum.

Workup

customsealed into a microwave tube
temperaturecooled to room temperature
concentrationThe reaction mixture was concentrated
dissolutiondissolved in DCM (10.00 mL)
customThe crude product was purified by ion exchange chromatography
washThe desired product was eluted from the column
customwere evaporated to dryness

Sources & evidence

ORD record: ord-8172f47ca2e448609599fcdf95219844
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101623B2

Reaction notes

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