Hydrochloride methanol → N-(5-Isoquinolyl)-1,4-butylenediamine hydrochloride

HRID 10510Notes

Reaction equation

HRID 10510 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][N:18]=[CH:19]2)=O)(C)(C)C.[ClH:24].CO>>[ClH:24].[CH:19]1[C:20]2[C:15](=[C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])[CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 21979821tert-Butyl {4-[(isoquinolin-5-yl)amino]butyl}carbamate

Product 1

HCID 21979782N-(5-Isoquinolyl)-1,4-butylenediamine hydrochloride

Procedure

According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 30 (316 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with methanol (1 ml) and diethyl ether (3 ml). The deposited precipitates were collected by filtration and washed with diethyl ether to obtain the title compound (276 mg) as light yellow powdery solid.

Workup

  1. custom(50° C., 2 hours)
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with methanol (1 ml) and diethyl ether (3 ml)
  4. customThe deposited precipitates
  5. filtrationwere collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-672a2fed6b53437e84c0e43685bb65b1
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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