1-Pyrrolidineethanamine → 1-{3-[Dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-propoxy}-3-(2-pyrrolidin-1-yl-ethylamino)-propan-2-ol

HRID 1046732Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][NH2:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][Si:10]([CH3:25])([CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:18][O:17]1>C(O)C>[CH3:25][Si:10]([CH3:9])([CH2:19][CH2:20][Si:21]([CH3:22])([CH3:24])[CH3:23])[CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([OH:17])[CH2:18][NH:8][CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-Pyrrolidin-1-yl-ethylamine (4.16 g; 36.4 mMol) and 40 mL of ethanol were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 2-{3-[Dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-propoxymethyl}-oxirane 8 (2 g; 7.28 mMol) mixed with 10 g ethanol was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. Ethanol was stripped off on the rotovap. The mixture was distilled under vacuum to remove impurities and excess 2-pyrrolidin-1-yl-ethylamine.

Workup

customequipped with a magnetic stirrer
customwas placed in an addition funnel
additionadded dropwise to the flask
stirringThe mixture was stirred
temperaturemaintained at 70° C. for an additional 4 hours
distillationThe mixture was distilled under vacuum
customto remove impurities and excess 2-pyrrolidin-1-yl-ethylamine

Sources & evidence

ORD record: ord-0147bc05326d4fa68d1c11de182d6ad8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569385B2

Reaction notes

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