Benzhydrylpiperazine → HCID 4163052, compound

HRID 1070757Notes

Reaction equation

HRID 1070757 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C1COCC1>[Cl:20][CH2:21][CH2:22][CH2:23][C:24]([N:17]1[CH2:18][CH2:19][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:16]1)=[O:25]

Participants

4

Reactant 2

HCID 70048BenzhydrylpiperazineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 4163052HCID 4163052, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

25 g (99 mmol) benzhydrylpiperazine and 15.2 ml (109 mmol) TEA are present in 200 ml absolute THF and cooled to ca. 0° C. under moisture exclusion. 14 g (99 mmol) 4-chlorobutyric chloride are dissolved in 40 ml absolute THF and added dropwise. The mixture is stirred an additional three hours at RT and subsequently filtered. The filtrate is concentrated under vacuum, the residue is taken up in acetic acid ethyl ester and washed with saturated NaCl solution. The organic phase is dried over sodium sulfate and concentrated under vacuum until dry. The resin is further processed without further purification: yield 35.1 g (99%).

Workup

  1. additionadded dropwise
  2. filtrationsubsequently filtered
  3. concentrationThe filtrate is concentrated under vacuum
  4. washwashed with saturated NaCl solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customuntil dry
  8. customThe resin is further processed without further purification

Sources & evidence

ORD record
ord-088793d339fc4538addb83f6e7a63476
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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