Hydrochloric Acid → Tert-butoxycarbonyl-N,N'-dimethyl hexane diamine

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Reaction Steps

Tert-butoxycarbonyl azide in ether ("Organic Synthesis V", p. 157-158) (2.9 g, 20 mmol, 5.2 ml) was added dropwise to a stirred solution of N,N'-dimethyl-hexane diamine (Aldrich Cat. No. D16110-1) (Beilstein 4(1), p. 422) (2.92 g, 20 mmol) in dimethyl sulphoxide (DMSO) (30 ml). The temperature was kept at 20° C. with external cooling. After the addition was complete (30 minutes), stirring was continued at room temperature for 1 hour, whereupon water (30 ml) was added. The solution was acidified (pH 5) with 2N HCl and extracted with ether (2 ×200 ml). The DMSO/water-mixture was made alkaline (pH 11) with 6N NaOH and extracted with ether (4×200 ml). Evaporation of the ether gave the title compound (1) (1.2 g) as a yellow oil.

Provenance & Evidence