Water → 3-(4-Methylpiperazin-1-yl)propyl (3-hydroxymethylphenyl)carbamate

HRID 655311Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

10 g (100 mmol) of N-methylpiperazine are added to a solution of 2.4 g (10 mmol) of 3-chloropropyl (3-hydroxymethylphenyl)carbamate in 10 ml of acetonitrile. The solution is refluxed for 4 h. The mixture is then hydrolysed by addition of water and cooled to about 65° C., and ethyl acetate is added. The mixture is then cooled to room temperature, during which the product is obtained as a solid between the organic and aqueous phases. The product is filtered off and rinsed with water, acetonitrile and ethyl acetate. The product is subsequently dried at 50° C. for several hours; ESI: 308 (M+H).

Workup

temperatureThe solution is refluxed for 4 h
temperatureThe mixture is then cooled to room temperature, during which the product
customis obtained as a solid between the organic and aqueous phases
filtrationThe product is filtered off
washrinsed with water, acetonitrile and ethyl acetate
customThe product is subsequently dried at 50° C. for several hours

Sources & evidence

ORD record: ord-3ca1c0a04ca14b9fa95cf584e2c6aea9
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071593B2

Reaction notes

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