Potassium Carbonate → 6-Benzyl-1,4-diazepan-6-ylamine

HRID 1367634Notes

Reaction equation

C([N:8]1[CH2:14][C:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([N+:15]([O-])=O)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].BrCC(OC(C)(C)C)=O>C(#N)C>[CH2:18]([C:13]1([NH2:15])[CH2:14][NH:8][CH2:9][CH2:10][NH:11][CH2:12]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 50 ml round-bottom flask the amine 5 (1.65 g 4.7 mmol) was dissolved in acetonitrile (15 ml) and K2CO3 (5.16 g, 37 mmol) was added. t-Butyl bromoacetate (4.55 g, 23.4 mmol) was slowly dropped into the stirred heterogeneous mixture, while maintaining the temperature <10° C. (ice bath). After the addition the mixture was heated at 60° C. with stirring until TLC showed complete conversion. The precipitate was filtered and washed with dichloromethane; the filtrate and the washings were combined and evaporated in vacuo to give the crude product. The semisolid residue was purified by silica gel chromatography (petroleum ether/ethyl acetate 9.3/0.7), obtaining pure 6 as pale yellow oil (1.35 g, 36%). ESI-MS: 832 (MNa+), 810 (MH+); (Calc. for C46H87N3O8: 809 u.m.a.).

Workup

temperaturewhile maintaining the temperature <10° C. (ice bath)
additionAfter the addition the mixture
filtrationThe precipitate was filtered
washwashed with dichloromethane
customevaporated in vacuo
customto give the crude product
customThe semisolid residue was purified by silica gel chromatography (petroleum ether/ethyl acetate 9.3/0.7)

Sources & evidence

ORD record: ord-bbb0c20971174a51b44c9f2c1cb27aeb
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893223B2

Reaction notes

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