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

HRID 22153

Reaction equation

HRID 22153 reaction equation
[C:1]([O:5][C:6](N=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOCC.[CH3:16][NH:17][CH:18]([NH:24][CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>CS(C)=O.O>[C:1]([O:5][C:6]([C:18]([NH:24][CH3:25])([NH:17][CH3:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 22571325N,N'-dimethyl-hexanediamine

Product 1

HCID 19927281Tert-butoxycarbonyl-N,N'-dimethyl hexane diamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. customwas kept at 20° C. with external cooling
  2. additionAfter the addition
  3. custom(30 minutes)
  4. additionwas added
  5. extractionextracted with ether (2 ×200 ml)
  6. extractionextracted with ether (4×200 ml)
  7. customEvaporation of the ether

Sources & evidence

ORD record
ord-4f37d6077a094a768fe4bf681ddb179d
Source dataset
uspto-grants-1995_06
Patent number
US05427779

Linked notes

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