Dichloromethane → HCID 131716830, compound

HRID 1656370Notes

Reaction equation

HRID 1656370 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]1.BrCC[O:19][C:20](=[O:33])[CH2:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][C:24]([CH3:32])([CH2:25]3)[CH2:23]1)[CH2:29]2.C(N(CC)CC)C.C(Cl)[Cl:42]>>[OH2:19].[ClH:42].[ClH:42].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:20](=[O:33])[CH2:21][C:22]23[CH2:29][CH:28]4[CH2:30][CH:24]([CH2:32][C:26]([CH3:25])([CH2:27]4)[CH2:31]2)[CH2:23]3)[CH2:9][CH2:8]1.[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:20](=[O:19])[CH2:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][C:24]([CH3:32])([CH2:25]4)[CH2:23]2)[CH2:29]3)[CH2:9][CH2:8]1.[ClH:42].[ClH:42]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 138853581-Piperazineethanamine, 4-(2-pyrimidinyl)-HCID 15124082HCID 15124082, compound

Product 1

HCID 131716830HCID 131716830, compound

Procedure

The title compound was prepared by stirring [4-(2-pyrimidinyl]piperazino]ethylamine (2.0 g, 0.009 mol), 3-methyladamantane-1-acetic acid bromoethyl ester (2.34 g, 0.01 mol) and triethylamine (1.0 g, 0.015 mol) in 50 mL of CH2Cl2 for 24 hours. The methylene chloride solution was washed with water, dried (anhydrous Na2SO4) and removed under reduced pressure. The remaining residue was subjected to preparative HPLC over silica gel column using ethyl acetate as the eluent and the desired product was separated and converted to the dihydrochloride hemihydrate salt with ethanolic HCl, m.p. 248°-251° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried (anhydrous Na2SO4)
  3. customremoved under reduced pressure
  4. customthe desired product was separated

Sources & evidence

ORD record
ord-63e8f817b4484615afe570e68641e668
Source dataset
uspto-grants-1993_10
Patent number
US05254552

Reaction notes

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