Dichloromethane → Hydrochloric Acid

HRID 1831422Notes

Reaction equation

HRID 1831422 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46](=[O:55])[N:47]([CH3:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:41][CH:40]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:64]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:36][CH2:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][C:46](=[O:55])[N:47]([CH3:54])[C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)=[CH:43][CH:44]=3)=[O:15])=[CH:16][CH:17]=2)[CH2:6][CH2:7]1.[ClH:64]

Participants

8

Reactant 6

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acidHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 2

HCID 313Hydrochloric AcidHCID 69519520HCID 69519520, compound

Procedure

A solution of 4-(4-methylpiperazinyl)methyl benzoic acid (0.3 mmol), EDAC (0.36 mmol) and triethylamine (1.0 mmol) in CH2Cl2 (10 mL) was added N-hydroxybenzoetriazole and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol). The mixture was stirred 16 h at rt and purified by preparative HPLC (Gilson) to give the title compound in 25% yield as its crystalline hydrochloride after treatment with HCl in diethyl ether.

Workup

  1. custompurified by preparative HPLC (Gilson)

Sources & evidence

ORD record
ord-918dbb5f3ab645c8b16247fdee18d14e
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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