3-(Butylamino)propan-1-ol → N-butyl-N-(3-hydroxypropyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea

HRID 648490Notes

Reaction equation

HRID 648490 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[CH2:24]([NH:28][CH2:29][CH2:30][CH2:31][OH:32])[CH2:25][CH2:26][CH3:27]>ClCCl>[CH2:24]([N:28]([CH2:29][CH2:30][CH2:31][OH:32])[C:2]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[S:3])[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 52612263-(Butylamino)propan-1-olHCID 155818991-(4-Isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine

Product 1

HCID 13732393N-butyl-N-(3-hydroxypropyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thioureaYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 parts of 1-(4-isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine, 6.3 parts of 3-(butylamino)-1-propanol and 130 parts of dichloromethane was stirred for 3 hours at room temperature. The reaction mixture was evaporated and the residue was triturated in 2-propanone. The product was filtered off and dried, yielding 12.7 parts (92%) of N-butyl-N-(3-hydroxypropyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea; mp. 153.9° C. (44).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated in 2-propanone
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-3ec3094c4f5f4ba1b3be8a3389793c0f
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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