Diisopropylethylamine → HCID 58504140, compound

HRID 2407661Notes

Reaction equation

HRID 2407661 reaction equation
Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][C:24]=1[O:32][CH3:33].O.ON1C2C=CC=CC=2N=N1.[NH2:45][CH2:46][CH:47]1[CH2:52][CH2:51][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][CH2:48]1>ClCCl>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:45][CH2:46][CH:47]2[CH2:52][CH2:51][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][CH2:48]2)=[O:29])=[CH:25][C:24]=1[O:32][CH3:33]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 20633784-Chloro-3-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 58504140HCID 58504140, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.26 g) and diisopropylethylamine (2.05 mL) were added to a room temperature solution of 4-chloro-3-methoxybenzoic acid (2.00 g) and 1-hydroxybenzotriazole hydrate (1.81 g) in dichloromethane (53 mL). After the reaction was stirred for five minutes, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (2.53 g) was added and the mixture was stirred overnight. The reaction was then partitioned between 1 N hydrochloric acid and dichloromethane. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated and purified by column chromatography on silica gel (dichloromethane:methanol=19:1). The resulting residue was triturated in diethyl ether and the solids were collected by filtration to obtain the title compound (3.56 g) having the following physical data. 1H NMR (DMSO-d6): δ 8.60 (t, J=5.7 Hz, 1H), 7.61-7.39 (m, 3H), 3.91 (m, 5H), 3.15 (t, J=6.0 Hz, 2H), 2.81-2.62 (m, 2H), 1.72-1.51 (m, 3H), 1.39 (s, 9H), 1.12-0.92 (m, 2H)+;

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was then partitioned between 1 N hydrochloric acid and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel (dichloromethane:methanol=19:1)
  7. customThe resulting residue was triturated in diethyl ether
  8. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-32fe08cd8a5b4d15a9866a918ddf1aad
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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