Hydrochloric Acid → 4-{5-[4-(2-aminoethyl)phenoxy]pentyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

HRID 1433290Notes

Reaction equation

HRID 1433290 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C@@H:29]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:30][CH2:31][N:32]([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH:23]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)C.[ClH:49]>ClCCl.C(OCC)C>[ClH:49].[ClH:49].[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C@@H:29]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:30][CH2:31][N:32]([CH:36]([CH3:37])[CH3:38])[CH:33]([CH3:34])[CH3:35])[CH:23]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 57933162tert-butyl(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)carbamate

Product 1

HCID 866164904-{5-[4-(2-aminoethyl)phenoxy]pentyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)carbamate (Preparation 58, 1.66 g, 2.69 mmol) was dissolved in dichloromethane (20 ml) and ethanol (3 ml) and hydrochloric acid (12 ml of a 2M solution in diethyl ether) was added, and the mixture stirred overnight at room temperature. Solvent was removed in vacuo and the residue dissolved in dichloromethane and solvent removed in vacuo again to furnish the title compound as a yellow foam, 1.6 g

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. customsolvent removed in vacuo again

Sources & evidence

ORD record
ord-cb7752e42b57417caba59a5f1dd757f0
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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