4-Pentylaniline → HCID 131727457, compound

HRID 1983563Notes

Reaction equation

HRID 1983563 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH2:24][CH3:25].Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[CH2:21]([C:26]1[CH:27]=[CH:28][C:29]([NH:30][C:18]([C@@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:20])=[CH:31][CH:32]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 931624-PentylanilineHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 131727457HCID 131727457, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (S)—N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (10.0 g, 36.1 mmol) and 4-pentylaniline (4.91 g, 30.1 mmol) in chloroform (150 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (6.92 g, 36.1 mmol). The reaction was allowed to proceed overnight and then washed with aqueous sodium bicarbonate solution, dried (sodium sulfate) and concentrated to afford crude product as an off-white, foamy solid. This material was used in the next step without further purification.

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customto afford crude product as an off-white, foamy solid
  5. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-9482b4b5a4ae40dfb03bf84b9df8d3f1
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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