1,2,3,4-Tetrahydro-1-naphthylamine → HCID 67358447, compound

HRID 1667091Notes

Reaction equation

HRID 1667091 reaction equation
[CH:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[O:12]=[C:13]1[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31](O)=[O:32].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:12]=[C:13]1[C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31]([NH:11][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:32]

Participants

5

Reactant 3

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 67358447HCID 67358447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydronaphthalen-1-amine (0.030 g, 0.204 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.060 g, 0.204 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.059 g, 0.306 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.05-7.31 (m, 14H), 5.98-6.03 (m, 1H), 5.05-5.13 (m, 1H), 4.08 (d, J=15.5 Hz, 1H), 4.05 (d, J=15.5 Hz, 1H), 3.51 (t, J=6.5 Hz, 2H), 2.78 (q, J=6.3 Hz, 2H), 2.71 (t, J=6.5 Hz, 2H), 1.85-1.97 (m, 1H), 1.56-1.78 (m, 2H), 1.45-1.55 (m, 1H); MS (ESI−) m/z 423 (M−H)−.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-d18e8e6025824b32a501868ae1607e80
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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