tert-butyl N-(4-aminobutyl)carbamate → N-[4-(benzhydryl-amino)-butyl]-carbamic acid tert-butyl ester

HRID 2251949Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].[CH:16](Br)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

5.0 g (26.6 mmol) N-(tert-butoxycarbonyl)-1,4-diaminobutane 5.5 g (39.8 mmol) potassium carbonate and 0.9 g (5.3 mmol) potassium iodide are placed in 50 ml DMF and 6.6 g (26.6 mmol) benzhydryl bromide are added dropwise at RT. The mixture is stirred for 12 hours at 70° C. and the suspension is filtered after cooling and the filtrate is concentrated under vacuum. The residue is taken up in 200 ml chloroform and washed with 100 ml water. The organic phase is dried over sodium sulfate and, subsequently, the solvent is removed under vacuum. The accumulated crude product is further processed without further purification: Yield 10.8 g.

Workup

filtrationthe suspension is filtered
temperatureafter cooling
concentrationthe filtrate is concentrated under vacuum
washwashed with 100 ml water
dry with materialThe organic phase is dried over sodium sulfate
customsubsequently, the solvent is removed under vacuum
customis further processed without further purification

Sources & evidence

ORD record: ord-7a24c81354fb4ad39b75757daf1225e2
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320993B1

Reaction notes

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