Hydrochloric Acid → N-benzyl-4-[(2R)-pyrrolidin-2-ylmethoxy]aniline

HRID 1909674Notes

Reaction equation

HRID 1909674 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>CO.C(OCC)C>[CH2:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44221317(R)-2-(4-Benzylamino-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 44129620N-benzyl-4-[(2R)-pyrrolidin-2-ylmethoxy]anilineYield 117.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To the product from step 1 (148 mg, 0.387 mmol) in methanol (3 mL) was added 1M HCl in diethyl ether (6 mL) and the resulting mixture was stirred at rt for 3 h. The solvent was removed in vacuo to obtain the title product as a solid (128 mg, 93%); MS; m/z 283 (M+H): LCMS (UV) 97%: Elemental analysis Calc C, 60.85; H, 6.81; N, 7.88; Found C, 57.26; H, 7.21; N, 7.24. 1H NMR (400 MHz, DMSO-d6) δ 1.60-1.73 (m, 1H), 1.87-2.12 (m, 3H), 3.17-3.21 (m, 2H), 3.84-3.87 (m, 2H), 4.19-4.23 (dd, 1H J1=3.6 Hz, J2=10.8 Hz), 4.11-4.16 (m, 1H), 4.44 (s, 2H), 7.0 (d, 2H J=8.8 Hz), 7.29-7.38 (m, 5H); 7.48-7.49 (m, 2H) 9.1 (s, 1H), 9.8 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d7c7b0bca5544d42b893f77f1fa1abfd
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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