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Youngman et al.
(m, 4H), and 8.70 (br s, 2H). MS: m/z 272 (MHþ). HRMS; C17H19ClN
Calcd. for 272.120602 (obs. 272.120501).
cis-1-Benzyl-6-chloro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride (1, R156-Cl, R25Ph). Prepared from 2 (R156-Cl) in the same
manner as 1 (R15H). 1H NMR (DMSO-d6): ꢀ 2.02 (m, 2H), 2.41 (t, 1H),
2.83–3.10 (m, 2H), 3.18 (d of d, 1H), 3.30 (m, 1H), 3.52–3.56 (m, 1H),
5.98 (d, 1H), 6.52 (d of d, 1H), 7.09 (d, 1H), 7.21–7.29 (m, 3H), and 8.62
(br s, 3H). MS: m/z 272 (MHþ). HRMS; C17H19ClN Calcd. for
272.120602 (obs. 272.121077).
cis-1-Benzyl-7-chloro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride (1, R157-Cl, R25Ph). Prepared from 2 (R157-Cl) in the same
1
manner as 1 (R15H). H NMR (DMSO-d6): ꢀ 2.02–2.11 (m, 2H), 2.41
(t, 1H), 2.80–2.92 (m, 1H), 2.97–3.05 (m, 1H), 3.20 (d of d, 1H), 3.34
(m, 1H), 3.53–3.63 (m, 1H), 5.90 (s, 1H), 7.09 (d, 2H), 7.14 (s, 2 H),
7.23–7.40 (m, 3H), and 8.63 (br s, 1H). MS: m/z 272 (MHþ). HRMS;
C17H19ClN Calcd. for 272.120602 (obs. 272.121018).
cis-1-Benzyl-8-chloro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride (1, R1 5 8-Cl, R2 5 Ph). Prepared from 2 (R1 5 8-Cl) in
the same manner as 1 (R1 5 H). 1H NMR (DMSO-d6): ꢀ 2.05–2.13
(m, 2H), 2.53 (m, 1H), 2.86–2.97 (m, 1H), 3.03–3.18 (m, 1H), 3.25 (d
of d, 1H), 3.48–3.58 (m, 1H), 3.81–3.87 (m, 1H), 6.93–6.97 (m, 2H),
7.02–7.07 (m, 1H), 7.12–7.17 (m, 5H), and 8.66 (br s, 3H). MS: m/z
272 (MHþ). HRMS; C17H19ClN Calcd. for 272.120602 (obs.
272.120898).
cis-1-Benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride (1, R1 5 6-OMe, R2 5 Ph). Prepared from 2 (R1 5 6-OMe) in the
same manner as 1 (R1 5 H). 1H NMR (CDCl3): ꢀ 2.05–2.30 (m, 2H),
2.50–2.60 (m, 1H), 2.83–3.03 (m, 3H), 3.30–3.40 (m, 2H), 3.71 (s, 3H),
6.00 (d, 1H), 6.35 (d of d, 1H), 6.60 (d, 1H), 7.02–7.16 (m, 5H), 8.53 (bs,
1H), and 8.96 (bs, 2H). MS: m/z (MHþ) 268. HRMS; C18H22NO Calcd. for
268.170140 (obs. 268.171181).
cis-1-Benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride (1, R1 5 6-F, R2 5 Ph). Prepared from 2 (R1 5 6-F) in the same
manner as 1 (R1 5 H). 1H NMR (DMSO-d6): ꢀ 1.96–2.13 (m, 2H), 2.40 (t,
1H), 2.82–3.12 (m, 2H), 3.17 (dd, 1H), 3.28–3.37 (m, 1H), 3.47–3.60 (br
m, 1H), 5.98 (m, 1H), 6.62 (m, 1H), 6.98 (m, 1H), 7.08 (d, 2H), 7.18–7.30
(m, 3H), and 8.64 (br s, 3H). MS: m/z 256 (MHþ). HRMS; C17H19FN
Calcd. for 256.150153 (obs. 256.150147).
cis-1-Allyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydro-
chloride(1, R156-OMe, R25CH5CH2). Prepared from 2 (R156-OMe) in
the same manner as 1 (R15H), substituting allyl bromide for benzyl
bromide. 1H NMR (DMSO-d6): ꢀ 1.91–2.10 (m, 3H), 2.54 (m, 1H),