Hydrochloric Acid → N-[(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride

HRID 387624Notes

Reaction equation

HRID 387624 reaction equation
[CH2:1]([C@H:8]([NH:26][C:27]([C:29]1[C:30]2[CH2:31][CH2:32][N:33]([CH:40]([CH2:44][CH2:45][CH3:46])[CH2:41][CH2:42][CH3:43])[C:34](=[O:39])[C:35]=2[CH:36]=[CH:37][CH:38]=1)=[O:28])[C@H:9]([OH:25])[CH2:10][NH:11][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:47]>C(OCC)C>[ClH:47].[CH2:1]([C@H:8]([NH:26][C:27]([C:29]1[C:30]2[CH2:31][CH2:32][N:33]([CH:40]([CH2:44][CH2:45][CH3:46])[CH2:41][CH2:42][CH3:43])[C:34](=[O:39])[C:35]=2[CH:36]=[CH:37][CH:38]=1)=[O:28])[C@H:9]([OH:25])[CH2:10][NH:11][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=2)[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25206287N-[(1S,2R)-1-Benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide

Product 1

HCID 25206286N-[(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

79 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved in 1.2 cm3 of ethyl ether at a temperature close to 20° C. 0.4 cm3 of a 2M hydrochloric acid solution in ethyl ether is added while stirring under argon, at a temperature of 5° C. The reaction mixture precipitates. The stirring is continued for 20 min, then is stopped in order to remove the supernatant. 5 cm3 of ethyl ether are again added. This operation is carried out twice. The last suspension is then concentrated under reduced pressure (5 kPa). 68 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a white solid.

Workup

  1. customclose to 20° C
  2. customThe reaction mixture precipitates
  3. customto remove the supernatant
  4. addition5 cm3 of ethyl ether are again added
  5. concentrationThe last suspension is then concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-b82994087915415390ed6a3a4d8b8c23
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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