Hydrochloric Acid → HCID 131727464, compound

HRID 883593Notes

Reaction equation

HRID 883593 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:12][CH:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[C:10]2[C:5](=[C:6]([CH3:23])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[K+].[Br-]>CO>[ClH:1].[CH3:2][N:3]1[CH2:12][CH:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[C:10]2[C:5](=[C:6]([CH3:23])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 689976452,8-Dimethyl-4-naphthalen-2-yl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 131727464HCID 131727464, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using ethereal HCl and methanol, the product from Step B (0.73 g, 2.5 mmol) was converted to its hydrochloride salt (136 mg, 17%, 98.4% AUC HPLC) as a white amorphous solid: mp 210-214° C.; 1H NMR (300 MHz, CD3OD) δ 7.76-7.90 (m, 4 H), 7.47-7.55 (m, 2 H), 7.26 (dd, J=8.6, 1.6 Hz, 1 H), 7.10-7.21 (m, 2 H), 6.77 (d, J=7.3 Hz, 1 H), 4.78 (dd, J=11.2, 6.0 Hz, 1H), 4.65 (d, J=15.7 Hz, 1 H), 4.48 (d, J=15.6 Hz, 1 H), 3.87 (dd, J=12.1, 6.0 Hz, 1 H), 3.66 (t, J=11.8 Hz, 1 H), 3.13 (s, 3 H), 2.36 (s, 3 H), IR (KBr) 3434, 2926, 2546, 1459, 754, 479 cm−1; Cl MS m/z 288 [C21H21N+H]+; Anal. Calcd. for C21H21N.HCl.0.5H2O: C, 75.77; H, 6.96; N, 4.21. Found: C, 76.04; H, 6.85; N, 4.14.

Sources & evidence

ORD record
ord-b003d116ce3944079677a75815baedb5
Source dataset
uspto-grants-2012_08
Patent number
US08236796B2

Reaction notes

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