(1-(2-Aminoethyl)piperidin-4-yl) (4-fluorophenyl) ketone → HCID 13851181, compound

HRID 978450Notes

Reaction equation

HRID 978450 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1.[N:19]([C:22]1[CH:32]=[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:23]=1[C:24](OCC)=[O:25])=[C:20]=[S:21]>O1CCCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([CH:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][N:1]3[C:24](=[O:25])[C:23]4[C:22](=[CH:32][C:31]([O:33][CH2:34][C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)=[CH:30][CH:29]=4)[NH:19][C:20]3=[S:21])[CH2:5][CH2:6]2)=[O:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3019268(1-(2-Aminoethyl)piperidin-4-yl) (4-fluorophenyl) ketoneHCID 20202879HCID 20202879, compound

Product 1

HCID 13851181HCID 13851181, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 6.25 parts of [1-(2-aminoethyl)-4-piperidinyl](4-fluorophenyl)methanone and 135 parts of tetrahydrofuran was added dropwise a solution of 7.5 parts of ethyl 2-isothiocyanato-4-(phenylmethoxy)benzoate in 45 parts of tetrahydrofuran. Upon completion, stirring was continued for 4 hours at room temperature and for 30 minutes at reflux temperature. After cooling, the product was filtered off and crystallized from a mixture of N,N-dimethylformamide and water. The product was filtered off and dried, yielding 3.8 parts (29%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-(phenylmethoxy)-2-thioxo-4(1H)-quinazolinone; 236.0° C. (dec.) (6).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe product was filtered off
  4. customcrystallized from a mixture of N,N-dimethylformamide and water
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-e03af632bb6249de9d0248c71e255c80
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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